Lithium borohydride → 4-Chloro-N-[4,4,4-trifluoro-1-hydroxymethyl-2-(2,2,2-trifluoroethyl)-butyl]-benzenesulfonamide

HRID 1987594Notes

Reaction equation

HRID 1987594 reaction equation
C[O:2][C:3](=O)[CH:4]([NH:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[CH:5]([CH2:11][C:12]([F:15])([F:14])[F:13])[CH2:6][C:7]([F:10])([F:9])[F:8].[Li+].[BH4-]>C1COCC1>[Cl:26][C:23]1[CH:24]=[CH:25][C:20]([S:17]([NH:16][CH:4]([CH2:3][OH:2])[CH:5]([CH2:6][C:7]([F:8])([F:9])[F:10])[CH2:11][C:12]([F:14])([F:13])[F:15])(=[O:18])=[O:19])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 575292742-(4-Chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester

Product 1

HCID 247659444-Chloro-N-[4,4,4-trifluoro-1-hydroxymethyl-2-(2,2,2-trifluoroethyl)-butyl]-benzenesulfonamideYield 67.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester (120 mg, 0.27 mmol) in THF (5 mL) was treated with LiBH4 (2M THF, 0.3 mL) for 18 hours at 25° C. The reaction was carefully quenched by the addition of 2M HCl and the organic solvent removed in vacuo. The aqueous layer was extracted with EtOAc (2×10 mL). The organic layers were combined, dried over Na2SO4 and evaporated to afford a crude oil which was purified by flash chromatography, eluting with 30:70 EtOAc:hexanes, to provide the title compound as a white solid (75 mg) in 67% yield. Mass Spectrum (−ESI): 412.0 (M−H)−.

Workup

  1. customThe reaction was carefully quenched by the addition of 2M HCl
  2. customthe organic solvent removed in vacuo
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. dry with materialdried over Na2SO4
  5. customevaporated
  6. customto afford a crude oil which
  7. customwas purified by flash chromatography
  8. washeluting with 30:70 EtOAc

Sources & evidence

ORD record
ord-a7266eb5c0634d379ac7aebb0007c9ce
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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