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

HRID 876421Notes

Reaction equation

HRID 876421 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][CH:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1

Participants

4

Reactant 2

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

Product 1

HCID 22933363tert-Butyl 4-hydroxyazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of tert-butyl 4-oxoazepane-1-carboxylate (0.60 g, 2.81 mmol), in MeOH (11 mL) was cooled to 0° C. NaBH4 (0.266 g, 7.03 mmol) was added and the mixture was slowly warmed to ambient temperature where the reaction stirred overnight. The mixture was concentrated in vacuo and the residue was taken up in EtOAc (20 mL) and saturated aqueous NH4Cl solution (20 mL) The layers were separated and the aqueous phase was extracted with EtOAc (2×10 mL) The combined organic extracts were washed with brine and dried over Na2SO4, then filtered and concentrated. The product was isolated as a thick colorless oil that solidified overnight to a white solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customsaturated aqueous NH4Cl solution (20 mL) The layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (2×10 mL) The combined organic extracts
  4. washwere washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe product was isolated as a thick colorless oil that solidified overnight to a white solid

Sources & evidence

ORD record
ord-172782db7262493f8630d289aa25e09d
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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