[4-(2-Cyclopropyl-2-phenyl-vinyl)-pyridin-2-yl]-carbamic acid tert-butyl ester → [4-(2-Cyclopropyl-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 1023433Notes

Reaction equation

HRID 1023433 reaction equation
[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[C:12]([CH:14]=[C:15]([CH:22]2[CH2:24][CH2:23]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.C(Cl)Cl.[Pd]>[C:1]([O:5][C:6](=[O:25])[NH:7][C:8]1[CH:13]=[C:12]([CH2:14][CH:15]([CH:22]2[CH2:23][CH2:24]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 77977979[4-(2-Cyclopropyl-2-phenyl-vinyl)-pyridin-2-yl]-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 69085979[4-(2-Cyclopropyl-2-phenyl-ethyl)-pyridin-2-yl]-carbamic acid tert-butyl esterYield 102.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

[4-(2-Cyclopropyl-2-phenyl-vinyl)-pyridin-2-yl]-carbamic acid tert-butyl ester (94 mg, 0.28 mmol) is dissolved in methanol (1.5 mL) and DCM (1.5 mL). Then 5% palladium on carbon (59 mg, 0.028 mmol) is added. The reaction is stirred for 16 hours under the hydrogen atmosphere. The palladium on carbon is filtered and the filtrate is concentrated to give 97 mg of the crude product which is used in the next step without purification.

Workup

  1. filtrationThe palladium on carbon is filtered
  2. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-cb5646d931b1455ba31b4b6ecf52d454
Source dataset
uspto-grants-2014_05
Patent number
US08722709B2

Reaction notes

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