Tetrahydrofuran → HCID 66877289, compound

HRID 503950Notes

Reaction equation

HRID 503950 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[OH:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].OS([O-])(=O)=O.[K+].[O-]S([O-])(=O)=O.[Na+].[Na+].C1C[O:48][CH2:47][CH2:46]1>>[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[O:29][CH2:46][CH2:47][OH:48])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 66877230HCID 66877230, compoundHCID 86586342KHSO4 Na2SO4

Product 1

HCID 66877289HCID 66877289, compoundYield 91%

Procedure

3-[4-(3-Fluoro-benzenesulfonyl)-2-hydroxy-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (120 mg) was dissolved in THF (2 mL) and lithiumborohydride (7.94 mg, 0.365 mmol) was added under argon atmosphere. The reaction mixture was stirred at room temperature for 6 hours, then cooled to 0-5° C. and a solution of 10% KHSO4/Na2SO4 was carefully added until pH 2 was reached. The resulting mixture was extracted with EtOAc, and the combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The resulting crude material was purified via flash chromatography (hexane/EtOAc, 1/1) to give 103 mg (91% yield) of 3-[4-(3-fluoro-benzenesulfonyl)-2-(2-hydroxy-ethoxy)-phenyl]-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. temperaturecooled to 0-5° C.
  2. extractionThe resulting mixture was extracted with EtOAc
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe resulting crude material was purified via flash chromatography (hexane/EtOAc, 1/1)

Sources & evidence

ORD record
ord-ccfc312d4d6143ce9f1e27d38a93c771
Source dataset
uspto-grants-2010_08
Patent number
US07776910B2

Reaction notes

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