Acetic Acid → HCID 10269810, compound

HRID 1372525Notes

Reaction equation

C([NH:4][C:5]1[C:17]([F:18])=[C:16]2[C:8]([C:9]3[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:23])[C:10]=3[C:24]([F:27])([F:26])[F:25])=[CH:7][C:6]=1[F:28])(=O)C.C(O)(=O)C.Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:4][C:5]1[C:17]([F:18])=[C:16]2[C:8]([C:9]3[C:14]([CH2:19][CH2:20][CH2:21][CH3:22])([CH2:15]2)[CH2:13][CH2:12][C:11](=[O:23])[C:10]=3[C:24]([F:27])([F:25])[F:26])=[CH:7][C:6]=1[F:28]

Participants

Conditions

Temperature: 100 °C

Procedure

The crude 7-(acetylamino)-9a-butyl-6,8-difluoro-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one from step 2 (about 0.318 mmol) was treated with acetic acid (2 mL) and 6N HCl (2 mL). The resulting solution was stirred and heated in an oil bath at 100° C. for 2 hours. After cooling to room temperature, the mixture was poured into a slurry of solid Na2CO3 in CH2Cl2, dried over MgSO4, then filtered through a pad of silica gel and the product washed off with EtOAc. The filtrate and washings were concentrated under vacuum. The crude product was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate, developing with 25% EtOAc in hexanes, to afford 7-amino-9a-butyl-6,8-difluoro-4-(trifluoromethyl)-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.026 g, 23%) as a yellow solid.

Workup

temperatureAfter cooling to room temperature
dry with materialdried over MgSO4
filtrationfiltered through a pad of silica gel
washthe product washed off with EtOAc
concentrationThe filtrate and washings were concentrated under vacuum
customThe crude product was purified by preparative layer chromatography on a 0.05×20×20 cm silica gel GF plate

Sources & evidence

ORD record: ord-e967c177bdc24459b82c6175a803c5d3
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157604B2

Reaction notes

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