Methanol → HCID 86732232, compound

HRID 930399Notes

Reaction equation

HRID 930399 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:19][S@@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH3:18])[CH2:10][C:11](OC(C)(C)C)=[O:12].[BH4-].[Li+].CO>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C:9]([NH:19][S@@:20]([C:22]([CH3:25])([CH3:24])[CH3:23])=[O:21])([CH2:10][CH2:11][OH:12])[CH3:18]

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 86732233HCID 86732233, compound

Product 1

HCID 86732232HCID 86732232, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl 3-(2,3-difluorophenyl)-3-((R)-1,1-dimethylethylsulfinamido)butanoate (17.9 g, 47.7 mmol) in THF (250 mL) at ambient temperature was added lithium borohydride, 2m solution in THF (47.7 mL, 95 mmol) followed by MeOH (12 mL, slightly exothermic reaction. added slowly via syringe). After stirred for 2 h, the reaction was carefully quenched by the addition of saturated ammonium chloride, followed by water and EtOAc. The separated organic phase was washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated and dried in vacuum to afford (R)-N-(2-(2,3-difluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide as light yellow foam. It was carried to next step without purification. MS m/z=306.1 [M+H]+. Calculated for C14H21F2NO2S: 305.4

Workup

  1. custom12 mL, slightly exothermic reaction
  2. additionadded slowly via syringe)
  3. customthe reaction was carefully quenched by the addition of saturated ammonium chloride
  4. washThe separated organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customdried in vacuum

Sources & evidence

ORD record
ord-9fa68c9fb9b344de8cc3871cb7735e6a
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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