Lithium borohydride → HCID 66877670, compound

HRID 503961Notes

Reaction equation

HRID 503961 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)(=[O:21])=[O:20])=[CH:15][C:14]=2[C:29](OCC)=[O:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([S:19]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([F:28])[CH:23]=3)(=[O:21])=[O:20])=[CH:15][C:14]=2[CH2:29][OH:30])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 66876536HCID 66876536, compound

Product 1

HCID 66877670HCID 66877670, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-[2-Ethoxycarbonyl-4-(3-fluoro-benzenesulfonyl)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (136 mg, 0.285 mmol) was dissolved in 25 ml of THF. LiBH4 (9.3 mg, 0.428 mmol) was added and the mixture was stirred at room temperature for 4 hours. The reaction was quenched by the addition of pH2 buffer and extracted with EtOAc. The combined extracts were dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (CH2Cl2/MeOH 95/5) to give 139 mg (quantitative) of 3-[4-(3-Fluoro-benzenesulfonyl)-2-hydroxymethyl-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a clear oil.

Workup

  1. customThe reaction was quenched by the addition of pH2 buffer
  2. extractionextracted with EtOAc
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash chromatography (CH2Cl2/MeOH 95/5)

Sources & evidence

ORD record
ord-84cca18889c24760913dbfcbb3d0df7f
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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