Sodium hydride → HCID 86596144, compound

HRID 2222925Notes

Reaction equation

[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[C:11]1(=[O:21])[O:15][CH2:14][CH:13]2[CH2:16][CH2:17][CH:18]3[CH2:20][CH:19]3[CH:12]12>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([S:10][CH2:14][CH:13]2[CH2:16][CH2:17][CH:18]3[CH:19]([CH2:20]3)[CH:12]2[C:11]([OH:21])=[O:15])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 110 °C

Procedure

To a suspension of NaH (165 mg, 4.05 mmol) in dry dimethylformamide (10 mL) under an atmosphere of dry nitrogen was added 4-fluorothiophenol (430 μL, 4.05 mmol) dropwise and the reaction was stirred for 15 min. A solution of (3αR/S,5αS/R,6αR/S,6βR/S)-octahydro-1H-cyclopropa[3,4]benzo[1,2-c]furan-1-one (202 mg, 1.35 mmol) in dry dimethylformamide (2 mL) was added to the reaction mixture and was heated to 110° C. for 4.5 h. The reaction mixture was cooled to room temperature and quenched with aqueous 10% HCl, the product extracted with ethyl acetate, and dried on anhydrous sodium sulfate. The solvent was removed in vacuo and the product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 2/8+0.5% AcOH) to afford the desired product (1R/S,2R/S,3R/S,6S/R)-3-{[(4-fluorophenyl)-sulfanyl]methyl}bicyclo[4.1.0]heptane-2-carboxylic acid.

Workup

temperatureThe reaction mixture was cooled to room temperature
customquenched with aqueous 10% HCl
extractionthe product extracted with ethyl acetate
dry with materialdried on anhydrous sodium sulfate
customThe solvent was removed in vacuo
customthe product was purified by flash chromatography over silica gel (ethyl acetate/hexanes, 2/8+0.5% AcOH)

Sources & evidence

ORD record: ord-4143431ad20b410aaaabd6fca8773a59
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371747B2

Reaction notes

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