HCID 131729029, compound → 2-Benzyl-6,7-dimethyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

HRID 1013377Notes

Reaction equation

HRID 1013377 reaction equation
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH:10]([C:11](=[CH2:20])[C:12]3[C:18]([CH3:19])=[CH:17][S:16][C:13]=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[CH2:15][CH:14]2[CH:10]([CH:11]([CH3:20])[C:12]3[C:18]([CH3:19])=[CH:17][S:16][C:13]=32)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 131729029HCID 131729029, compound

Product 1

HCID 597894662-Benzyl-6,7-dimethyl-1,2,3,3a,7,7a-hexahydro-4-thia-2-aza-cyclopenta[alpha]pentalene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of product from step g) (3.1 g) in MeOH (55 ml) was treated with 10% Pd/C (4.65 g) and a balloon of H2 at 40° C. for 16 hours. The reaction mixture was filtered through a pad of celite, evaporated in vacuo and the residue purified by silica-gel chromatography using a ethyl acetate/hexanes gradient (0% to 50% ethyl acetate) to give 948 mg (49% over two steps) of the subtitle product. MS calculated for C18H21NS+H 284, observed 284.

Workup

  1. filtrationThe reaction mixture was filtered through a pad of celite
  2. customevaporated in vacuo
  3. customthe residue purified by silica-gel chromatography

Sources & evidence

ORD record
ord-bf7d8ae4a59f4249aaa4d09c1c41ff5a
Source dataset
uspto-grants-2011_07
Patent number
US07981919B2

Reaction notes

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