Sodium borohydride → HCID 54573955, compound

HRID 1872267Notes

Reaction equation

HRID 1872267 reaction equation
[CH:1]([O:14][NH:15][C:16]([CH:18]1[CH:24]([C:25](=[O:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH:22]=[CH:21][CH2:20][N:19]1[S:33]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)(=[O:35])=[O:34])=[O:17])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.ClCCl>[CH:1]([O:14][NH:15][C:16]([CH:18]1[CH:24]([CH:25]([OH:32])[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:23][CH:22]=[CH:21][CH2:20][N:19]1[S:33]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)(=[O:35])=[O:34])=[O:17])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54214489HCID 54214489, compound

Product 1

HCID 54573955HCID 54573955, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
0 °C

Procedure

3-Benzoyl-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid benzhydryloxy-amide (32 mg, 0.054 mmoL) was dissolved in a methanol:dichloromethane (3:1, 1.3 mL) mixture and cooled to 0° C. This solution was treated with sodium borohydride and stirred 5 hrs at 0 to 25° C. The solvents were removed in vacuo and the residue was reconstituted in dichloromethane. This solution was washed with 1 M aqueous HCl, and H2O, dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 1.25% methanol in dichloromethane) to give 3-(hydroxy-phenyl-methyl)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid benzhydryloxy-amide; MS: (M+H)+ 598.8, (M+NH4)+ 615.7.

Workup

  1. customThe solvents were removed in vacuo
  2. washThis solution was washed with 1 M aqueous HCl, and H2O
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (silica, 1.25% methanol in dichloromethane)

Sources & evidence

ORD record
ord-a1d106e01ae24afe8e14e44421248ce7
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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