Lithium borohydride → 3,4,5-trifluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzene sulfonamide

HRID 1987588Notes

Reaction equation

HRID 1987588 reaction equation
C([O:3][C:4](=O)[CH:5]([NH:15][S:16]([C:19]1[CH:24]=[C:23]([F:25])[C:22]([F:26])=[C:21]([F:27])[CH:20]=1)(=[O:18])=[O:17])[CH:6]([C:11]([F:14])([F:13])[F:12])[C:7]([F:10])([F:9])[F:8])C.[Li+].[BH4-]>C1COCC1>[F:25][C:23]1[CH:24]=[C:19]([S:16]([NH:15][CH:5]([CH2:4][OH:3])[CH:6]([C:7]([F:10])([F:8])[F:9])[C:11]([F:12])([F:13])[F:14])(=[O:17])=[O:18])[CH:20]=[C:21]([F:27])[C:22]=1[F:26]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 866160084,4,4-Trifluoro-2-(3,4,5-trifluoro-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester

Product 1

HCID 247659453,4,5-trifluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzene sulfonamideYield 30.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
25 °C

Procedure

To a solution of 4,4,4-trifluoro-2-(3,4,5-trifluoro-benzenesulfonylamino)-3-trifluoromethyl-butyric acid ethyl ester (0.54 g, 1.207 mmol) in THF (10 mL) was added LiBH4 in THF (2.40 mL, 4.81 mmol) at 0° C. The reaction was allowed to warm to 25° C. for 19 h. The reaction was cooled to 0° C., quenched with 2N HCl (slow addition), and diluted with Et2O (40 mL). The organic layer was washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (15 mL), dried over MgSO4, filtered and concentrated to obtain a crude oil (0.49 g). The crude product was purified by Biotage Flash™ chromatography, eluent: 1:7 EtOAc-hexanes, to afford 3,4,5-trifluoro-N-(3,3,3-trifluoro-1-hydroxymethyl-2-trifluoromethyl-propyl)-benzene sulfonamide as a white solid (0.150 g, 29.6%). Mass Spectrum (+ESI): 422 [M+H]+.

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched with 2N HCl (slow addition)
  3. additiondiluted with Et2O (40 mL)
  4. washThe organic layer was washed sequentially with 1N aqueous HCl (10 mL), saturated aqueous NaHCO3 (10 mL) and brine (15 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto obtain a crude oil (0.49 g)
  9. customThe crude product was purified by Biotage Flash™ chromatography, eluent

Sources & evidence

ORD record
ord-006a04f27819405f82941c8514e1c12c
Source dataset
uspto-grants-2009_06
Patent number
US07550629B2

Reaction notes

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