Reaktion #6172

ord-d2fd2c20c66545699c81e6c81df4e199

Reaktionsgleichung

CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C
alcohol
CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C
(2R,3S)-N-[(tert-Butyloxy) carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol
→
CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C
title compound
Ausbeute 67.0%
CC(C)[Si](O[C@@H](CO)[C@H](CC1CCCCC1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C
(2R,3S)-N-[(tert-Butyloxy) carbonyl]-3-amino-4-cyclohexyl-2-(triisopropylsilyloxy) butan-1-ol
Ausbeute 67.0%

Edukte

CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C
alcohol
CC(C)[Si](O[C@@H](CO)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C)(C(C)C)C(C)C
(2R,3S)-N-[(tert-Butyloxy) carbonyl]-3-amino-4-phenyl-2-(triisopropylsilyloxy) butan-1-ol

Reagenzien

Keine

Lösungsmittel

CO
MeOH
[Rh]
Rh/C

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    EinengenThe filtrate was concentrated
  2. 2
    Sonstigepurified by medium pressure column chromatography (silica gel, 15% ethyl acetate in hexane)

Vorschrift

The alcohol of Step 2 (12.8 g, 29.3 mmol) was dissolved in MeOH (135 mL) and hydrogenated with 5% Rh/C at 60 psi and 60° C. for 30 hours. The filtrate was concentrated and purified by medium pressure column chromatography (silica gel, 15% ethyl acetate in hexane) to give the title compound as a white solid (8.70 g, 67% yield, mp 61°-63° C.). Anal. calcd. for C24H49NO4Si: C, 64.96; H, 11.13; N, 3.16. Found: C, 65.16; H, 11.26; N, 3.12.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246969uspto-grants-1993_09