Reaction #1771992

ord-90b328bac4b043ef9af773bd138bac58

Reaction equation

C=CCC1(C)C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1
N-tertbutoxycarbonyl-4-allyl-4-methylproline
→
CCCC1(C)C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1
N-tert-butoxycarbonyl 4-propyl-4-methylproline

Reactants

C=CCC1(C)C[C@@H](C(=O)O)N(C(=O)OC(C)(C)C)C1
N-tertbutoxycarbonyl-4-allyl-4-methylproline

Reagents

[Pd]
Pd 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 N-tertbutoxycarbonyl-4-allyl-4-methylproline (400 mg, 1.48 mmol) (see Example II Step 4) and 10% Pd on carbon (400 mg) in methanol (20 mL) was hydrogenated at 50 psi for 4 hours. The mixture was filtered and concentrated.

Source

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