HCID 70665177, compound → HCID 70664739, compound

HRID 1026652Notes

Reaction equation

HRID 1026652 reaction equation
[CH2:1]([N:8]1[CH2:16][C@H:15]2[C@:10]([CH3:25])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19]([C:22]([CH3:24])=[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]([CH3:25])([CH2:11][CH2:12][C:13]3[C:20]([Cl:21])=[C:19]([CH:22]([CH3:23])[CH3:24])[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 70665177HCID 70665177, compound

Product 1

HCID 70664739HCID 70664739, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A suspension of cis-2-benzyl-6-chloro-3a-methyl-7-(prop-1-en-2-yl)-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (0.156 mmol, 55 mg) and 5% Pd—C (7.81 μmol, 16.63 mg) in MeOH (3 ml) was stirred under H2 atmosphere (1 bar, multiple hydrogenator) at ° C. for 1.5 h and then passed through Whatman membrane filter. The resulting filtrate was concentrated in vacuo a crude solid that was redissolved in MeOH (3 ml) and further 5% Pd—C (7.81 μmol, 16.63 mg) was added. The resulting suspension was stirred under H2 atmosphere (balloon) at 20° C. for 3 h and then passed through Whatman membrane. The filtrate was concentrated to give cis-2-benzyl-6-chloro-7-isopropyl-3a-methyl-2,3,3a,4,5,9b-hexahydro-1H-benzo[e]isoindole (46.6 mg), m/z=354.2 [M+H]+.

Workup

  1. filtrationfilter
  2. concentrationThe resulting filtrate was concentrated in vacuo a crude solid
  3. dissolutionthat was redissolved in MeOH (3 ml)
  4. stirringThe resulting suspension was stirred under H2 atmosphere (balloon) at 20° C. for 3 h
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-27f04dbda2904b4981a82ae4fe9c3446
Source dataset
uspto-grants-2014_05
Patent number
US08729274B2

Reaction notes

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