Reaktion #1117350

ord-06a3a96b054e4a028de0fe8005591ba2

Reaktionsgleichung

CC(C)(C)OC(=O)N1CCC[C@H]1CO
(2S)-1-t-butoxycarbonyl-2-hydroxymethylpyrrolidine
COc1ccc(CS)cc1
4-methoxybenzyl mercaptan
[H-].[Na+]
sodium hydride
CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O
(2S)-1-t-butoxycarbonyl-2-methanesulfonyloxymethylpyrroldine
→
COc1ccc(CSC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1
title compound
COc1ccc(CSC[C@@H]2CCCN2C(=O)OC(C)(C)C)cc1
(2S)-1-t-Butoxycarbonyl-2-(4-methoxybenzylthiomethyl)pyrrolidine

Edukte

CC(C)(C)OC(=O)N1CCC[C@H]1CO
(2S)-1-t-butoxycarbonyl-2-hydroxymethylpyrrolidine
COc1ccc(CS)cc1
4-methoxybenzyl mercaptan
[H-].[Na+]
sodium hydride
CC(C)(C)OC(=O)N1CCC[C@H]1COS(C)(=O)=O
(2S)-1-t-butoxycarbonyl-2-methanesulfonyloxymethylpyrroldine

Reagenzien

Keine

Lösungsmittel

CN(C)C=O
dimethylformamide

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe procedure described in preparation 5-(2)

Vorschrift

The procedure described in preparation 5-(2) was repeated, but using 12.16 g of (2S)-1-t-butoxycarbonyl-2-methanesulfonyloxymethylpyrroldine [prepared by the methanesulfonylation of (2S)-1-t-butoxycarbonyl-2-hydroxymethylpyrrolidine], 7.3 ml of 4-methoxybenzyl mercaptan and 2.3 g of sodium hydride (as a 55% w/w suspension in mineral oil) in 100 ml of dry dimethylformamide, to afford 13.93 g of the title compound as an oil.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05104867uspto-grants-1992_04