4-(Benzyloxy)butan-2-one → 2-(4-Benzyloxy-2-Butylamino)-1-(4-Hydroxy-3-Methylsulfinylphenyl)Ethanol

HRID 1701863Notes

Reaction equation

HRID 1701863 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11](=O)[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([S:25]([CH3:27])=[O:26])[CH:19]=1)[OH:17].C([BH3-])#N.[Na+]>CO>[CH2:1]([O:8][CH2:9][CH2:10][CH:11]([NH:14][CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([S:25]([CH3:27])=[O:26])[CH:19]=1)[OH:17])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 2345114-(Benzyloxy)butan-2-oneHCID 5003444Sodium cyanoborohydrideHCID 205052872-Amino-1-(4-hydroxy-3-methylsulfinylphenyl)ethanol

Product 1

HCID 541898642-(4-Benzyloxy-2-Butylamino)-1-(4-Hydroxy-3-Methylsulfinylphenyl)Ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Combine 4-benzyloxy-2-butanone (1.78 g, 10 mmol) with 2-amino-1-(4-hydroxy-3-methylsulfinylphenyl)ethanol (10 mmol) in methanol (50 ml) and add sodium cyanoborohydride (0.63 g, 10 mmol). Let stand 16 hours, concentrate the solution and purify the crude product by chromatography on silica gel using chloroform: methanol: ammonium hydroxide (70:27:3) as eluent to obtain the title compound.

Workup

  1. concentrationconcentrate the solution
  2. custompurify the crude product by chromatography on silica gel

Sources & evidence

ORD record
ord-d7b6ee01dd9b48e2b995ab6f3100a7cc
Source dataset
uspto-grants-1983_04
Patent number
US04379166

Reaction notes

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