Acetic Acid → 7-amino-9a-butyl-4-ethyl-6,8-difluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one

HRID 1372527Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

The crude diketone from step 1 (about 1.05 mmol) was treated with acetic acid (5 mL) and 6N HCl (5 mL). The resulting solution was stirred and heated in an oil bath at 100° C. for 1.5 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 30% EtOAc in hexanes, to afford 7-amino-9a-butyl-4-ethyl-6,8-difluoro-1,2,9,9a-tetrahydro-3H-fluoren-3-one (0.16 g, 48%) 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-6220b20dd5d84c0686181bf100a49d3e
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07157604B2

Reaction notes

Loading…