Production Method 1

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  5 °C; 1 h, rt

Reference

Preparation of azoles containing sulfone

, European Patent Organization, , ,

Production Method 2

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  rt → -5 °C; 1 h, rt
1.2 Reagents: Acetic acid

Reference

Substituted spiro-amide compounds as bradykinin receptor 1 inhibitors and their preparation and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 3

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  -5 °C → rt; 1 h, rt

Reference

Preparation of spirocyclic amides as bradykinin receptor modulators

, World Intellectual Property Organization, , ,

Production Method 4

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  rt → -5 °C; 1 h, rt
1.2 Reagents: Acetic acid

Reference

Preparation of pyrimidinylsulfonamides as b1 bradykinin receptor (b1r) inhibitors for the treatment of pain

, World Intellectual Property Organization, , ,

Production Method 5

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; 1.5 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water

Reference

Tetrahydroisoquinoline spiro compound as PRMT5 inhibitor

, World Intellectual Property Organization, , ,

Production Method 6

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  cooled; overnight, rt
1.2 Reagents: Sodium sulfate Solvents: Water ;  rt

Reference

Protein inhibitor or degrading agent, pharmaceutical composition containing same and pharmaceutical use

, World Intellectual Property Organization, , ,

Production Method 7

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  0 °C; 12 h, 20 °C
1.2 Reagents: Ammonium chloride Solvents: Water ;  20 °C

Reference

Preparation of heterobifunctional compounds as CDK2 degraders and uses thereof

, World Intellectual Property Organization, , ,

Production Method 8

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  -10 °C; 12 h, 25 °C
1.2 Reagents: Water

Reference

Preparation of benzothiazole derivatives as IRAK degraders and uses thereof

, World Intellectual Property Organization, , ,

Production Method 9

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Ethanol ;  cooled; rt; 3 h, rt
1.2 Reagents: Water ;  rt
1.3 Reagents: Ammonium chloride Solvents: Water ;  pH 7, rt

Reference

Preparation of 6-nitro-2,3-dihydroimidazo[2,1-b]oxazole derivatives as mycobacterium tuberculosis drugs

, China, , ,

Production Method 10

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Cerium trichloride Solvents: Methanol ;  rt → -78 °C
1.2 Reagents: Sodium borohydride ;  -78 °C; -78 °C → -20 °C; 30 min, -20 °C
1.3 Reagents: Water

Reference

Preparation of novel 3-aza-spiro[5.5]undecane derivatives as monoamine neurotransmitter re-uptake inhibitors

, World Intellectual Property Organization, , ,

Production Method 11

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  -5 °C; 1 h, rt
1.2 Reagents: Acetic acid ;  rt
1.3 Reagents: Water

Reference

Substituted benzimidazoles, benzothiazoles and benzoxazoles as bradykinin 1 receptor inhibitors and their preparation and use in the treatment of diseases

, World Intellectual Property Organization, , ,

Production Method 12

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  -5 °C; 1 h, rt

Reference

Preparation of spirocyclic indoles as bradykinin receptor modulators

, World Intellectual Property Organization, , ,

Production Method 13

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  rt → -5 °C; 1 h, rt
1.2 Reagents: Acetic acid

Reference

Substituted pyrimidine and triazine compounds as bradykinin receptor 1 inhibitors useful in the treatment of pain and other disorders

, United States, , ,

Production Method 14

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Tetrahydrofuran ;  -5 °C; 1 h, rt

Reference

Preparation of disulfonamides as bradykinin receptor modulators

, World Intellectual Property Organization, , ,

Production Method 15

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; 1.5 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water ;  rt

Reference

Preparation of tetrahydroisoquinoline compounds for treatment of diseases mediated by PRMT5

, World Intellectual Property Organization, , ,

Production Method 16

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  rt; 1 h, rt

Reference

Pyrimidopyrazole compounds as fourth generation EGFR inhibitors

, World Intellectual Property Organization, , ,

Production Method 17

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  0 °C; 20 min, 0 °C; 1 h, 0 °C
1.2 Reagents: Ammonium chloride Solvents: Water
1.3 Reagents: Hydrochloric acid Solvents: Water ;  pH 7

Reference

Bruton's tyrosine kinase degrader containing fused-ring or spiro-ring

, World Intellectual Property Organization, , ,

Production Method 18

873924-08-4

918644-73-2

Reaction Conditions

1.1 Reagents: Sodium borohydride Solvents: Methanol ;  1 h, rt

Reference

Spirocyclic compounds for treatment of Obesity and Diabetes

, World Intellectual Property Organization, , ,

Production Method 19

918644-73-2

Reaction Conditions

Reference

3-aza-spiro[5.5]undecane derivatives and their use as monoamine neurotransmitter re-uptake inhibitors

, United States, , ,

tert-butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate Raw materials

• Tert-butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

tert-butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate Preparation Products

• tert-butyl 9-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate (918644-73-2)

• 1. Acetylcholinesterase amperometric detection system based on a cobalt(II) tetraphenylporphyrin-modified electrode
  Analyst, 1996,121, 1123-1126
• 2. An atom efficient route to N-aryl and N-alkyl pyrrolines by transition metal catalysis?
  Supaporn Sawadjoon,Joseph S. M. Samec Org. Biomol. Chem., 2011,9, 2548-2554
• 3. An atlas of endohedral Sc2S cluster fullerenes?
  Li-Hua Gan,Rui Wu,Jian-Lei Tian,Patrick W. Fowler Phys. Chem. Chem. Phys., 2017,19, 419-425
• 4. An integrated system for field analysis of Cd(ii) and Pb(ii) via preconcentration using nano-TiO2/cellulose paper composite and subsequent detection with a portable X-ray fluorescence spectrometer?
  Xiaofeng Lin RSC Adv., 2016,6, 9002-9006
• 5. An alumina stabilized graphene oxide wrapped SnO2 hollow sphere LIB anode with improved lithium storage?
  Xiang Liu,Qian Sun,A. B. Djuri?i?,Maohai Xie,Baohu Dai,Jinyao Tang,Charles Surya,Changzhong Liao,Kaimin Shih RSC Adv., 2015,5, 100783-100789

• 2680528-18-9(tert-butyl 9-hydroxy-9-methyl-3-azaspiro5.5undecane-3-carboxylate)
• 183170-69-6(tert-butyl 4-(1-hydroxyethyl)piperidine-1-carboxylate)
• 240401-28-9(Tert-butyl 2-hydroxy-7-azaspiro[3.5]nonane-7-carboxylate)
• 358625-61-3(tert-butyl 4-(2-hydroxy-2-methylpropyl)piperidine-1-carboxylate)
• 2306271-83-8(tert-butyl 10-hydroxy-3-azaspiro[5.5]undecane-3-carboxylate)
• 919360-50-2(tert-butyl 4-(3-hydroxybutyl)piperidine-1-carboxylate)
• 1126084-33-0(tert-butyl 4-(2-hydroxypropyl)piperidine-1-carboxylate)
• 810686-40-9(1-PIPERIDINECARBOXYLIC ACID, 4-BUTYL-4-HYDROXY-, 1,1-DIMETHYLETHYL ESTER)
• 1206830-71-8(tert-butyl 4-(1R)-1-hydroxyethylpiperidine-1-carboxylate)
• 374794-88-4(1-Piperidinecarboxylic acid, 4-hydroxy-4-(3-hydroxypropyl)-,1,1-dimethylethyl ester)