Benzyl Bromide → cis-2-benzyl-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

HRID 382816Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[C@H:14]3[C@H:9]([CH2:10][CH2:11][NH:12][CH2:13]3)[CH2:8][C:7](=[O:15])[C:6]=2[CH:16]=1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([N:12]1[CH2:11][CH2:10][C@H:9]2[C@H:14]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:16][C:6]=3[C:7](=[O:15])[CH2:8]2)[CH2:13]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Reactant 2

HCID 7498Benzyl Bromide

HCID 86757545cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

Product 1

HCID 86757548cis-2-benzyl-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one

Procedure

In an analogous manner to that described in Example 49 b), from cis-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one by alkylation with benzyl bromide there was obtained cis-2-benzyl-8-fluoro-1,3,4,4a,5,10b-hexahydro-2H-benzo[h]isoquinolin-6-one, which was converted with MeOH/HCl into the hydrochloride with m.p. >220°.

Sources & evidence

ORD record: ord-38164eb1d710406fbb663af5d452fd9a
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310208B1

Reaction notes

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