(4-Tert-butyl-benzyl)-[2-(3-ethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester → HCID 68558247, compound

HRID 19797Notes

Reaction equation

HRID 19797 reaction equation
[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[CH:17])[CH:11]=1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:29])[N:7]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:21][CH:20]=1)[CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH2:16][CH3:17])[CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 86613993(4-Tert-butyl-benzyl)-[2-(3-ethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester

Product 1

HCID 68558247HCID 68558247, compoundYield 48.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (4-tert-butyl-benzyl)-[2-(3-ethynyl-phenyl)-ethyl]-carbamic acid tert-butyl ester (149 mg, 0.381 mmol) in methanol (12 ml) was stirred at RT under an atmosphere of hydrogen in the presence of a catalytic amount of palladium on charcoal (5%) for 2 days. The reaction mixture was then filtered and evaporated and the remaining residue was purified by chromatography (heptane/EtOAc 100:0 to 95:5) to obtain the title compound as a colorless oil (73 mg, 48%). MS (ISP) 396.4 (M+H)+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customevaporated
  3. customthe remaining residue was purified by chromatography (heptane/EtOAc 100:0 to 95:5)

Sources & evidence

ORD record
ord-b4db7203d5a54a6db04249c85c804ef3
Source dataset
uspto-grants-2010_06
Patent number
US07745477B2

Reaction notes

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