Sodium borohydride → Methyl 5-(3-((3R)-3-((E)-3-hydroxy-4-(3-(trifluoromethyl)phenyl)but-1-en-1-yl)-1,1-dioxidoisothiazolidin-2-yl)propyl)thiophene-2-carboxylate

HRID 524366Notes

Reaction equation

HRID 524366 reaction equation
[BH4-].[Na+].[O:3]=[S:4]1(=[O:36])[CH2:8][CH2:7][C@H:6](/[CH:9]=[CH:10]/[C:11](=[O:23])[CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[CH:14]=2)[N:5]1[CH2:24][CH2:25][CH2:26][C:27]1[S:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:28]=1>CO>[OH:23][CH:11]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]([F:20])([F:21])[F:22])[CH:14]=1)/[CH:10]=[CH:9]/[C@H:6]1[CH2:7][CH2:8][S:4](=[O:3])(=[O:36])[N:5]1[CH2:24][CH2:25][CH2:26][C:27]1[S:31][C:30]([C:32]([O:34][CH3:35])=[O:33])=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 118688788(R,E)-Methyl 5-(3-(1,1-dioxido-3-(3-oxo-4-(3-(trifluoromethyl)phenyl)-but-1-en-1-yl)isothiazolidin-2-yl)propyl)thiophene-2-carboxylate

Product 1

HCID 118677369Methyl 5-(3-((3R)-3-((E)-3-hydroxy-4-(3-(trifluoromethyl)phenyl)but-1-en-1-yl)-1,1-dioxidoisothiazolidin-2-yl)propyl)thiophene-2-carboxylateYield 9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium tetrahydridoborate (22 mg, 0.58 mmol) was added to a solution of the enone 12 (268 mg, 0.52 mmol) in MeOH (3.0 mL) at 0° C. The reaction was gradually allowed to warm to room temperature and stirred an additional 5 h. The solvent was removed in vacuo. The residue was partitioned between EtOAc and saturated aqueous ammonium chloride. The organic portion was separated then washed with brine, dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by flash column chromatography (silica gel, 3:1 EtOAc/hex) afforded 24 mg (9%) of pure alcohol 13.

Workup

  1. customThe solvent was removed in vacuo
  2. customThe residue was partitioned between EtOAc and saturated aqueous ammonium chloride
  3. customThe organic portion was separated
  4. washthen washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customPurification of the residue by flash column chromatography (silica gel, 3:1 EtOAc/hex)

Sources & evidence

ORD record
ord-86b7840dcd484bb1b39795bd8e9da073
Source dataset
uspto-grants-2016_05
Patent number
US09340534B2

Reaction notes

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