Sodium borohydride → HCID 59350854, compound

HRID 1644752Notes

Reaction equation

HRID 1644752 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([C:15](=[O:26])[C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:27])[CH:11]=2)[CH:6]=1.[BH4-].[Na+]>CO>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5]1[CH:14]=[C:13]([CH:15]([OH:26])[C:16]2[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:27])[CH:11]=2)[CH:6]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66775532HCID 66775532, compound

Product 1

HCID 59350854HCID 59350854, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of [6-fluoro-4-(4-methanesulfonyl-benzoyl)-naphthalen-2-yl]-acetic acid methyl ester (103.5 mg, 0.26 mmol) (example 2-1, 4th step) in methanol (3 mL) was added sodium borohydride (30 mg, 0.78 mmol) at room temperature. The reaction mixture was stirred at room temperature overnight, and then partitioned between ethyl acetate and water. The collected organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (RediSep® Flash column, 230-400 mesh, 0-40% ethyl acetate in hexane) gave {6-fluoro-4-[hydroxy-(4-methanesulfonyl-phenyl)-methyl]-naphthalen-2-yl}-acetic acid methyl ester (90 mg, 86%) as a yellow oil. MS (ESI+) cald. for C21H19FO5S 402 [(M+H)+], obsd. 403.

Workup

  1. custompartitioned between ethyl acetate and water
  2. dry with materialThe collected organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b089d25a6e54b71a5f8089f07dfe6a5
Source dataset
uspto-grants-2012_02
Patent number
US08124629B2

Reaction notes

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