Sodium Methoxide → Trans-2-methyl-7-(trifluoromethoxy)-1,2,3,3a,4,5-hexahydrobenzo[c]pyrrolo[3,4-e]azepin-6(10bH)-one

HRID 84948Notes

Reaction equation

[NH2:1][CH2:2][C@H:3]1[CH2:7][N:6]([CH3:8])[CH2:5][C@@H:4]1[C:9]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[C:10]=1[C:11](OC)=[O:12].C[O-].[Na+]>CO>[CH3:8][N:6]1[CH2:7][C@@H:3]2[C@H:4]([C:9]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[C:10]=3[C:11](=[O:12])[NH:1][CH2:2]2)[CH2:5]1

Participants

Conditions

Temperature: 70 °C

Procedure

The product obtained from Example 110B (5.5 g) was dissolved in 25 mL of methanol and treated with 5 mL of 25 weight % sodium methoxide in methanol. The reaction was stirred and heated at 70° C. for 16 hours. The reaction was cooled and concentrated, and the residue was purified via flash chromatography on a silica gel column (95:5 dichloromethane:2 N ammonia in methanol) to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 2.04-2.20 (m, 1H) 2.41 (s, 3H) 2.62 (dd, J=10.85 Hz, 8.82 Hz, 1H) 2.73 (t, J=8.31 Hz, 1H) 2.93-3.01 (m, 3H) 3.03-3.14 (m, 2H) 7.24 (d, J=7.80 Hz, 1H) 7.32 (d, J=8.14 Hz, 1H) 7.51-7.59 (m, 1H) 8.33 (t, J=5.76 Hz, 1H); MS (DCI+) m/z 301.1 [M+H]+.

Workup

temperatureThe reaction was cooled
concentrationconcentrated
customthe residue was purified via flash chromatography on a silica gel column (95:5 dichloromethane:2 N ammonia in methanol)

Sources & evidence

ORD record: ord-f3c654f78d904ef9b111f3be614c5ddb
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846951B2

Reaction notes

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