[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester → [4-(3,3-Dimethyl-butyl)-phenyl]-carbamic acid tert-butyl ester

HRID 1069185Notes

Reaction equation

HRID 1069185 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]#[C:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C1COCC1.CO>[C:1]([O:5][C:6](=[O:20])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:14][CH2:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 54041145[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 53872103[4-(3,3-Dimethyl-butyl)-phenyl]-carbamic acid tert-butyl esterYield 94.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-carbamic acid tert-butyl ester (37b, 2.50 g, 9.15 mmol) was treated with 1:1 THF/MeOH (50 mL) and Pd/C (0.5 g, 10%), shaken for 15.8 hours under an atmosphere of H2 (51.4 psi). More Pd/C (0.5 g, 20%) was added and the reaction was stirred for an additional 1.13 hours, then filtered and concentrated. The crude material was chromatographed on silica gel eluting with 1:9 EtOAc/Hexane to give 2.39 g (94%) of the desired product.

Workup

  1. stirringthe reaction was stirred for an additional 1.13 hours
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe crude material was chromatographed on silica gel eluting with 1:9 EtOAc/Hexane

Sources & evidence

ORD record
ord-2632df77fd1d42a08f7795cf60bdddb0
Source dataset
uspto-grants-2001_06
Patent number
US06251919B1

Reaction notes

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