Triethylamine → (2S,4S)-1-t-butoxycarbonyl-4-methylsulfonyloxy-2-methoxycarbonylpyrrolidine

HRID 1034520Notes

Reaction equation

HRID 1034520 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:25][S:26](Cl)(=[O:28])=[O:27]>ClCCl>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][S:26]([CH3:25])(=[O:28])=[O:27])[CH2:10][C@H:9]1[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 10752873N-Boc-cis-4-hydroxy-L-proline methyl ester

Product 1

HCID 14772681(2S,4S)-1-t-butoxycarbonyl-4-methylsulfonyloxy-2-methoxycarbonylpyrrolidine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a manner similar to Step A-3 in Preparative Example 7-A, (2S,4S)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine in dichloromethane is mesylated with triethylamine and methanesulfonylchloride in a nitrogen atmosphere under ice cooling to give (2S,4S)-1-t-butoxycarbonyl-4-methanesulfonyloxy-2-meth-oxycarbonylpyrrolidine. mp. 90.0° to 91.5° C.

Sources & evidence

ORD record
ord-598633395f1a4bac922e90e740311ba2
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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