Water → 7-(4-Amino-3-benzyloxybenzyl)-azepan-2-one

HRID 660552Notes

Reaction equation

HRID 660552 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:21]=[CH:22][C:23]=1[N+:24]([O-])=O)[CH2:12][CH:13]1[NH:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.O.[Sn](Cl)Cl.O>CCOC(C)=O>[NH2:24][C:23]1[CH:22]=[CH:21][C:11]([CH2:12][CH:13]2[NH:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:10][C:9]=1[O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 61436Stannous chloride dihydrateHCID 688400327-(3-Benzyloxy-4-nitrobenzyl)-azepan-2-one

Product 1

HCID 688389577-(4-Amino-3-benzyloxybenzyl)-azepan-2-one

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-(3-benzyloxy-4-nitrobenzyl)-azepan-2-one (600 mg, 1.7 mmol) in EtOAc (20 mL) is added tin (II) chloride dihydrate. The mixture is stirred at RT for 18 h then water is added. The mixture is extracted with EtOAc and the organic phase is washed with water and brine. The solution is dried over sodium sulfate and the solvent removed under reduced pressure to give the title compound: (M+1)+=325.

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. washthe organic phase is washed with water and brine
  3. dry with materialThe solution is dried over sodium sulfate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-ea1ec72e51394fd29c28b93c64dd624f
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Reaction notes

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