Hydrochloric Acid → 4-acetyl-7-amino-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372522Notes

Reaction equation

C([NH:4][C:5]1[CH:17]=[C:16]2[C:8]([C:9]3[C:14]([CH2:18][CH2:19][CH2:20][CH3:21])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:22])[C:10]=3[C:23]([O:25]CC)=[CH2:24])=[CH:7][C:6]=1[F:28])(=O)C.Cl>CO>[C:23]([C:10]1[C:11](=[O:22])[CH2:12][CH2:13][C:14]2([CH2:18][CH2:19][CH2:20][CH3:21])[C:9]=1[C:8]1[C:16](=[CH:17][C:5]([NH2:4])=[C:6]([F:28])[CH:7]=1)[CH2:15]2)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 7-(acetylamino)-9a-butyl-4-(1-ethoxyvinyl)-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (205 mg, 0.53 mmol) in methanol (7.5 mL) was treated with aqueous 6N HCl (7.5 mL). The resulting mixture was placed under a N2 atmosphere and stirred with heating in an oil bath at 80° C. for 50 minutes. After cooling to room temperature, the mixture was partitioned between EtOAc and aqueous 5% NaHCO3. The organic solution was washed with water and brine, dried over MgSO4, filtered, and evaporated under vacuum to afford 4-acetyl-7-amino-9a-butyl-6-fluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (157 mg, 93%) as a foam.

Workup

temperatureAfter cooling to room temperature
customthe mixture was partitioned between EtOAc and aqueous 5% NaHCO3
washThe organic solution was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
customevaporated under vacuum

Sources & evidence

ORD record: ord-3c082cd72ee0469f810f55da322bd4a3
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157604B2

Reaction notes

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