Reaction #1771993

ord-40794a691015423f8f8e6dd4b847146a

Reaction equation

CC(C)(C)OC(=O)N1CC(c2ccccc2)C[C@H]1C(=O)O
Boc-4-phenylproline
→
CC(C)(C)OC(=O)N1CC(C2CCCCC2)C[C@H]1C(=O)O
product
Yield 95.4%
CC(C)(C)OC(=O)N1CC(C2CCCCC2)C[C@H]1C(=O)O
Boc-4-cyclohexylproline
Yield 95.4%

Reactants

CC(C)(C)OC(=O)N1CC(c2ccccc2)C[C@H]1C(=O)O
Boc-4-phenylproline

Reagents

[Rh]
Rh on carbon

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe mixture was filtered
  2. 2
    Concentrationconcentrated

Procedure

A solution of the commercially available Boc-4-phenylproline (750 mg) and 5% Rh on carbon (750 mg) in methanol (15 mL) was hydrogenated at 50 psi for 24 hours. The mixture was filtered and concentrated to give 730 mg of product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: USRE043298E1uspto-grants-2012_04