4-Bromo-2-chloro-N,N-diethylbenzamide → (3aR,9bS)-tert-Butyl 6-chloro-4-methyl-5-oxo-8-propyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate

HRID 2100593Notes

Reaction equation

HRID 2100593 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[NH:9][C@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@H:7]3[C:6]=2[CH:5]=[C:4]([CH2:23][CH2:24][CH3:25])[CH:3]=1.Br[C:27]1C=CC(C(N(CC)CC)=O)=C(Cl)C=1>>[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH3:27])[C@H:8]3[CH2:13][N:14]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:15][C@@H:7]3[C:6]=2[CH:5]=[C:4]([CH2:23][CH2:24][CH3:25])[CH:3]=1

Participants

3

Reactant 2

HCID 161159314-Bromo-2-chloro-N,N-diethylbenzamideHCID 69054699(3aR,9bS)-tert-butyl 6-chloro-5-oxo-8-propyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate

Product 1

HCID 69057014(3aR,9bS)-tert-Butyl 6-chloro-4-methyl-5-oxo-8-propyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate

Procedure

Following the procedure described in Example 15, Part A, (3aR,9bS)-tert-butyl 6-chloro-5-oxo-8-propyl-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]isoquinoline-2(9bH)-carboxylate, the first eluting compound from Example 23, Part J, was converted into the title compound. LRMS (ESI): 379.17/381.15 (M+H)+.

Sources & evidence

ORD record
ord-55adb6805237496c86957255c7aa434b
Source dataset
uspto-grants-2009_08
Patent number
US07572805B2

Reaction notes

Loading…