Methanol → Capryloyl proline

HRID 1720519Notes

Reaction equation

HRID 1720519 reaction equation
C([O:8][C:9](=[O:24])[C@@H:10]1[CH2:14][CH2:13][CH2:12][N:11]1[C:15](=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])C1C=CC=CC=1.CO>O.[Pd]>[C:15]([N:11]1[CH2:12][CH2:13][CH2:14][C@H:10]1[C:9]([OH:24])=[O:8])(=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 2

HCID 887MethanolHCID 53996545N-octanoyl-L-proline benzyl ester

Product 1

HCID 18632639Capryloyl prolineYield 99.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

To a solution of N-octanoyl-L-proline benzyl ester (7.04 g) in 1% water-containing methanol (70 ml) was added 10% Pd-C (0.71 g), and the mixutre was stirred under hydrogen atmosphere at room temperature for 1.5 hours. After the catalyst was filtered off, the filtrate was concentrated to give 5.08 g of the title compound.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1f11259e02a84f41a64a9d273c3fed9f
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

Loading…