Methanol → tert-Butyl 4-hydroxyazepane-1-carboxylate

HRID 1808736Notes

Reaction equation

HRID 1808736 reaction equation
CO.[O:3]=[C:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]1.[BH4-].[Na+]>ClCCl>[OH:3][CH:4]1[CH2:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 887MethanolHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 4311764Sodium borohydride

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a methanol (250 mL) solution of tert-butyl 4-oxoazepane-1-carboxylate (18.1 g, 85.0 mmol) at 0° C. was added sodium borohydride (8.01 g, 212 mmol). The reaction mixture was stirred for 2 hours before concentration in vacuo. The residue was dissolved in dichloromethane (250 mL) and washed with brine. The precipitate was removed by filtration, and the filtrate was dried (magnesium sulfate), filtered and concentrated in vacuo to afford the title compound. 1H NMR (500 MHz, CDCl3) 3.87 (br s, 1H), 3.49-3.18 (m, 4H), 2.05-1.48 (m, 6H), 1.46 (s, 9H); LC-MS: m/z 238.2 (M+Na).

Workup

  1. washwashed with brine
  2. customThe precipitate was removed by filtration
  3. dry with materialthe filtrate was dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-52bdbb4d79854552a1464602888daf05
Source dataset
uspto-grants-2013_01
Patent number
US08361994B2

Reaction notes

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