Formaldehyde → (3aR,10bS)-8-Fluoro-2,5-dimethyl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bH)-one

HRID 84951Notes

Reaction equation

HRID 84951 reaction equation
C=O.[CH:3](C1C=C(C=CC=1)C(OC)=O)=O.Cl.[F:16][C:17]1[CH:18]=[CH:19][C:20]2[C@H:26]3[CH2:27][NH:28][CH2:29][C@@H:25]3[CH2:24][N:23]([CH3:30])[C:22](=[O:31])[C:21]=2[CH:32]=1>>[F:16][C:17]1[CH:18]=[CH:19][C:20]2[C@H:26]3[CH2:27][N:28]([CH3:3])[CH2:29][C@@H:25]3[CH2:24][N:23]([CH3:30])[C:22](=[O:31])[C:21]=2[CH:32]=1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 639145Methyl 3-formylbenzoateHCID 67167606(3aR,10bS)-8-fluoro-5-methyl-1,2,3,3a,4,5-hexahydrobenzo[c]pyrrolo[3,4-e]azepin-6(10bH)-one hydrochloride

Product 1

HCID 54673983(3aR,10bS)-8-Fluoro-2,5-dimethyl-1,2,3,3a,4,5-hexahydrobenzo[e]pyrrolo[3,4-c]azepin-6(10bH)-one

Procedure

The title compound was prepared according to the procedure outlined in Example 68 substituting formaldehyde for methyl 3-formylbenzoate and substituting (3aR,10bS)-8-fluoro-5-methyl-1,2,3,3a,4,5-hexahydrobenzo[c]pyrrolo[3,4-e]azepin-6(10bH)-one hydrochloride (Example 225B) for Example 2. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.46 (dt, J=16.6, 8.3, 1H), 7.27 (td, J=8.5, 2.8, 1H), 7.18 (dd, J=8.5, 5.6, 1H), 3.36 (ddd, J=19.2, 14.5, 5.7, 3H), 3.15-2.92 (m, 5H), 2.71 (dt, J=25.9, 9.0, 2H), 2.41 (d, J=6.1, 3H), 2.24-2.07 (m, 1H); MS (ESI+) m/z 249.1 [M+H]+.

Sources & evidence

ORD record
ord-d557a7299d6b4aaf8477c723aa3f5d7c
Source dataset
uspto-grants-2014_09
Patent number
US08846951B2

Reaction notes

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