N-Boc-hexahydro-1H-azepin-4-one → tert-Butyl 4-hydroxyazepane-1-carboxylate

HRID 1689822Notes

Reaction equation

HRID 1689822 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO.C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([OH:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 4311764Sodium borohydride

Product 1

HCID 22933363tert-Butyl 4-hydroxyazepane-1-carboxylateYield 94.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1 g (4.69 mmol) of 4-oxo-azepane-1-carboxylic acid tert-butyl ester), in 2 mL of Methanol and 8 mL of THF, is added at 0° C. (ice bath) sodium tetrahydroborate (0.18 g, 4.69 mmol). The resulting mixture is stirred at 0° C. for 1 h. To the reaction mixture is added at 0° C. (ice bath), a solution of HCl (1N) (2 mL), then solvent is removed and the resulting slurry is diluted with water and extracted with EtOAc (250 mL). The organic layers are combined, dried (Na2SO4), filtered and concentrated to afford the title compound as a colorless oil (0.95 g, 94%). MS (m/e): 216 (M+1).

Workup

  1. additionTo the reaction mixture is added at 0° C. (ice bath)
  2. customa solution of HCl (1N) (2 mL), then solvent is removed
  3. additionthe resulting slurry is diluted with water
  4. extractionextracted with EtOAc (250 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-dad877088770466aac0cc2e3584169dd
Source dataset
uspto-grants-2012_04
Patent number
US08153624B2

Reaction notes

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