HCID 70664461, compound → HCID 70664607, compound

HRID 1026653Notes

Reaction equation

HRID 1026653 reaction equation
[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@:10]([CH3:24])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19]([CH:22]=[CH2:23])[CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([N:8]1[CH2:16][C@@H:15]2[C@:10]([CH3:24])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19]([CH2:22][CH3:23])[CH:18]=[CH:17][C:14]=32)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 70664461HCID 70664461, compound

Product 1

HCID 70664607HCID 70664607, compoundYield 77.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
20 °C

Procedure

A suspension of trans-2-benzyl-6-chloro-3a-methyl-7-vinyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.095 mmol, 32 mg) and 5% Pd—C (4.74 μmol, 10.08 mg) in MeOH (3 ml) was stirred under H2 atmosphere (1 bar, multiple hydrogenator) at 20° C. for 1.5 h. The suspension was then passed through a Whatman membrane filter and the resulting filtrate was concentrated in vacuo to afford trans-2-benzyl-6-chloro-7-ethyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (24.9 mg), m/z=340.2 [M+H]+.

Workup

  1. filtrationfilter
  2. concentrationthe resulting filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-a5f4f3f589ca454697fab3a1e54cf24a
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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