Sodium borohydride → HCID 131734827, compound

HRID 1778532Notes

Reaction equation

HRID 1778532 reaction equation
[CH2:1]([N:8]1[CH:13]2[CH:14]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[CH2:15][CH:9]1[CH2:10][C:11](=[O:24])[CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([N:8]1[CH:13]2[CH:14]([O:16][Si:17]([C:20]([CH3:22])([CH3:21])[CH3:23])([CH3:18])[CH3:19])[CH2:15][CH:9]1[CH2:10][CH:11]([OH:24])[CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21699649HCID 21699649, compound

Product 1

HCID 131734827HCID 131734827, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 86a (6.9 g, 20 mmol, 1.0 eq) in MeOH (100 mL) was added NaBH4 (1.5 g, 40 mmol, 2.0 eq) slowly at room temperature, then the mixture was stirred at room temperature for 1 h. The mixture was quenched with water (100 mL), extracted with EA (100 mL) two times. The organic layer was combined, dried over Na2SO4 and concentrated to give 8-benzyl-6-[tert-butyl(dimethyl)silyl]oxy-8-azabicyclo[3.2.1]octan-3-ol 116b as a colorless oil, 6.24 g, yield: 90%. MS: calc'd (MH+) 348, measured (MH+) 348.

Workup

  1. customThe mixture was quenched with water (100 mL)
  2. extractionextracted with EA (100 mL) two times
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-19ea2f05fd9e42ef9b0f18df72c92e1a
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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