tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylate → tert-Butyl 3-hydroxy-8-azabicyclo(3.2.1)octane-8-carboxylate

HRID 473813Notes

Reaction equation

HRID 473813 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:10][CH:9]2[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:6]([CH2:7][CH2:8]2)[CH2:5]1>C(O)C>[OH:3][CH:4]1[CH2:5][CH:6]2[N:11]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:9]([CH2:8][CH2:7]2)[CH2:10]1

Participants

4

Reactant 2

HCID 2794767tert-Butyl 3-oxo-8-azabicyclo(3.2.1)octane-8-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 21187725tert-Butyl 3-hydroxy-8-azabicyclo(3.2.1)octane-8-carboxylateYield 92.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (178 mg, 4.7 mmol) was added to a solution of tert-butyl 3-oxo-8-azabicyclo[3.2.1]octane-8-carboxylate (0.50 g, 2.2 mmol) in ethanol (10 mL), and the resulting mixture was stirred at room temperature for one hour. The mixture was quenched with saturated ammonium chloride solution (30 mL), and extracted with ethyl acetate (3×20 mL). The combined extract was washed with water then brine, dried over sodium sulfate, filtered and concentrated to give tert-butyl 3-hydroxy-8-azabicyclo[3.2.1]octane-8-carboxylate (463 mg, 92% yield) as a mixture of endo and exo stereoisomers. GC-MS (EI) for C12H21NO3: 227 (M+).

Workup

  1. customThe mixture was quenched with saturated ammonium chloride solution (30 mL)
  2. extractionextracted with ethyl acetate (3×20 mL)
  3. extractionThe combined extract
  4. washwas washed with water
  5. dry with materialbrine, dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-055c6452b73d4bd5be429038e5891796
Source dataset
uspto-grants-2014_01
Patent number
US08637499B2

Reaction notes

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