Water → HCID 53877205, compound

HRID 1738903Notes

Reaction equation

HRID 1738903 reaction equation
[BH4-].[Na+].[C:3]1([CH:13]([OH:22])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[NH2:21])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[Si:23]([O:40][CH2:41][C:42]([CH3:46])([CH3:45])[CH:43]=O)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O>C(O)(=O)C>[C:3]1([CH:13]([OH:22])[C:14]2[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:15]=2[NH:21][CH2:43][C:42]([CH3:46])([CH3:45])[CH2:41][O:40][Si:23]([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 10936741HCID 10936741, compoundHCID 54464060HCID 54464060, compound

Product 1

HCID 53877205HCID 53877205, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium borohydride (1.73 g, 45.8 mmol) was added portionwise to a solution of α-(1-naphthyl)-2-amino-5-chlorobenzyl alcohol (9.76 g, 34.4 mmol) and 3-tert-butyldiphenylsilyloxy-2,2-dimethylpropanal (12.89 g, 37.9 mmol) in acetic acid (105 ml) at 0° C. The reaction mixture was allowed to warm to room temperature, and stirring was continued for 45 min. Hydrolysis with water was followed by repeated extraction of the mixture with ethyl acetate. The combined organic layers were washed with 1 N sodium hydroxide and dried with MgSO4. The filtrate was concentrated under reduced pressure, and the residue was purified by flash chromatography (hexane/ethyl acetate 9:1) to give the title compound (12.01 g, 57%) as a colorless oil.

Workup

  1. extractionextraction of the mixture with ethyl acetate
  2. washThe combined organic layers were washed with 1 N sodium hydroxide
  3. dry with materialdried with MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography (hexane/ethyl acetate 9:1)

Sources & evidence

ORD record
ord-af55ac8c6890495a86b1a1eb579671c2
Source dataset
uspto-grants-1999_10
Patent number
US05965553

Reaction notes

Loading…