Sodium borohydride → HCID 22137849, compound

HRID 858323Notes

Reaction equation

HRID 858323 reaction equation
C1COCC1.C(O)C.C[O:10][C:11](=O)[C:12]1[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[C:14]([NH:22][C:23](=[O:32])[CH2:24][S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:13]=1.[BH4-].[Na+]>C(OCC)(=O)C>[OH:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:22][C:23](=[O:32])[CH2:24][S:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 69592521HCID 69592521, compound

Product 1

HCID 22137849HCID 22137849, compoundYield 54.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

To a THF/ethanol (10:1) solution of 3-(2-Phenylsulfanyl-acetylamino)-5-trifluoromethyl-benzoic acid methyl ester (252 mg, 0.68 mmol) was added sodium borohydride (46 mg, 1.4 mmol), and the mixture was stirred at 65° C. for 2 hours. The reaction mixture was left overnight. The mixture was diluted with ethyl acetate, washed with 1 N HCl (2×) and brine. The organic layer was dried over MgSO4, filtered and stripped. The crude product was purified by flash chromatography on silica gel eluted with hexane/ethyl acetate (4:1) to give 126 mg of N-(3-Hydroxymethyl-5-trifluoromethyl-phenyl)-2-phenylsulfanyl-acetamide in 54% yield.

Workup

  1. waitThe reaction mixture was left overnight
  2. washwashed with 1 N HCl (2×) and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customThe crude product was purified by flash chromatography on silica gel
  6. washeluted with hexane/ethyl acetate (4:1)

Sources & evidence

ORD record
ord-ca1cf9c457354d2799745b1a5296c2a7
Source dataset
uspto-grants-2006_12
Patent number
US07148259B1

Reaction notes

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