Sodium Hydroxide → N-Boc-cis-4-hydroxy-L-proline methyl ester

HRID 1034519Notes

Reaction equation

HRID 1034519 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13]C=O)[CH2:10][C@H:9]1[C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:16]([O:18][CH3:19])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10707397HCID 10707397, compound

Product 1

HCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl esterYield 89.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4S)-1-t-butoxycarbonyl-4-formyloxy-2-methoxycarbonylpyrrolidine (5.12 g: 18.7 mmole) in methanol (51.0 ml), aqueous 1N-sodium hydroxide (18.7 ml) is added under ice cooling. The mixture is stirred at the same temperature for 20 minutes to give (2S,4S)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine (4.09 g). Yield: 89%. Colorless crystals. NMR δ(CDCl3) ppm: 1.44(d, J=8.2 Hz, 9H), 2.0 to 2.2(m, 1H), 2.2 to 2.5(m, 1H), 3.2 to 3.8(m, 3H), 3.79(d, J=2.8 Hz, 3H), 4.2 to 4.5(m, 2H). IR ν (KBr) cm-1 : 3460, 1728, 1677.

Sources & evidence

ORD record
ord-27459061a65545c5aad1b5241bd7d7a1
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

Loading…