Benzyloxyamine hydrochloride → tert-Butyl 4-aminoazepane-1-carboxylate

HRID 16202Notes

Reaction equation

HRID 16202 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.C(O[NH2:25])C1C=CC=CC=1.C([O-])(=O)C.[NH4+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([NH2:25])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 102312Benzyloxyamine hydrochlorideHCID 517165Ammonium AcetateHCID 1512679N-Boc-hexahydro-1H-azepin-4-one

Product 1

HCID 18946151tert-Butyl 4-aminoazepane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of N-(tert-butoxycarbonyl)-hexahydro-1H-azepin-4-one (0.5 g, 2.34 mmoles), O-benzylhydroxylamine hydrochloride (0.41 g, 2.57 mmoles) and ammonium acetate (0.45 g, 5.86 mmoles) in methanol (10 mL) was refluxed for 1.2 hours. The solvent was evaporated in vacuo and the crude oxime was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50). The product was taken in 4N NH3 in methanol (10 mL) and added 10% by weight Pd/C (100 mg) and stirred over H2 at balloon pressure for twelve hours. The reaction was filtered through a pad of celite and filtrate evaporated in vacuo to provide the title compound.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude oxime was purified by flash column chromatography (hexanes:ethyl acetate 100:0 to 50:50)
  3. additionadded 10% by weight Pd/C (100 mg)
  4. filtrationThe reaction was filtered through a pad of celite and filtrate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-ef639e8403424da3a9b48ea36e8f9895
Source dataset
uspto-grants-2010_06
Patent number
US07737137B2

Reaction notes

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