(Iodomethyl)cyclopentane → HCID 69018823, compound

HRID 1437963Notes

Reaction equation

I[CH2:2][CH:3]1[CH2:7][CH2:6][CH2:5][CH2:4]1.[C:8]1([N:14]2[C:22](=[O:23])[C:21]3[C@@H:20]4[C:24]([CH3:26])([CH3:25])[C@@:17]([CH3:27])([CH2:18][CH2:19]4)[C:16]=3[NH:15]2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>ClCCl>[CH:3]1([CH2:2][N:15]2[C:16]3[C@:17]4([CH3:27])[C:24]([CH3:26])([CH3:25])[C@@H:20]([CH2:19][CH2:18]4)[C:21]=3[C:22](=[O:23])[N:14]2[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (iodomethyl)cyclopentane (prepared according to W. L. Corbett US 20040067939; 352 mg, 1.68 mmol) and (4R,7S)-2-phenyl-7,8,8-trimethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 6; 90 mg, 0.34 mmol) was heated in an oil-bath at 100° C. for 6 days. The reaction mixture was allowed to cool and it was then diluted with dichloromethane (200 mL) and washed with water (5×30 mL), aqueous sodium thiosulfate solution (2×30 mL) and brine (30 mL). The organic extract was dried (magnesium sulfate), filtered, evaporated, and the residue purified on an Isco 40 g column, eluting with 30-100% ethyl acetate/hexanes and then held under high vacuum to give (4R,7S)-1-(cyclopentyl)methyl-7,8,8-trimethyl-2-phenyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (4.5 mg, 4%) as a semi-solid. ES(+)-MS (M+H) 351.

Workup

temperatureto cool
washwashed with water (5×30 mL), aqueous sodium thiosulfate solution (2×30 mL) and brine (30 mL)
extractionThe organic extract
dry with materialwas dried (magnesium sulfate)
filtrationfiltered
customevaporated
customthe residue purified on an Isco 40 g column
washeluting with 30-100% ethyl acetate/hexanes

Sources & evidence

ORD record: ord-f23bc32e00d14ea58d41112b945ce0fa
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07622492B2

Reaction notes

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