Methanol → HCID 86732270, compound

HRID 930432Notes

Reaction equation

HRID 930432 reaction equation
[Cl: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>O1CCCC1>[Cl: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 90372969HCID 90372969, compound

Product 1

HCID 86732270HCID 86732270, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (5)-tert-butyl 3-(2-chloro-3-fluorophenyl)-3-((R)-1,1-dimethylethylsulfinamido)butanoate (8.75 g, 22.33 mmol) in tetrahydrofuran (100 mL) was added lithium borohydride, 2.0M in THF (29.9 mL, 59.8 mmol) dropwise, followed by MeOH (7.05 mL, 174 mmol). The reaction was stirred for 40 min and was carefully quenched by the addition of saturated ammonium chloride (75 mL), followed by water (100 mL) and EtOAc. The separated organic phase was washed with brine, dried over sodium sulfate and filtered to give (R)-N-((S)-2-(2-chloro-3-fluorophenyl)-4-hydroxybutan-2-yl)-2-methylpropane-2-sulfinamide as a white solid (7.2 g, 100% yield). MS m/z=322 [M+H]+. Calculated for C14H21ClFNO2S: 321.8.

Workup

  1. customwas carefully quenched by the addition of saturated ammonium chloride (75 mL)
  2. washThe separated organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered

Sources & evidence

ORD record
ord-9b488949258e4c0cb9e1d4f0a43ef7fc
Source dataset
uspto-grants-2016_03
Patent number
US09296734B2

Reaction notes

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