Reaktion #48646

ord-eaad4f159d36464ea4a6575a5d404f59

Reaktionsgleichung

CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1COCc1ccccc1
5-(S)-benzyloxymethyl-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester
→
CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1CO
desired compound
CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1CO
2-(S)-(2-Cyclohexylethyl)-5-(S)-hydroxymethylmorpholine-4-carboxylic acid tert-butyl ester

Edukte

CC(C)(C)OC(=O)N1C[C@H](CCC2CCCCC2)OC[C@@H]1COCc1ccccc1
5-(S)-benzyloxymethyl-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester

Reagenzien

[OH-].[OH-].[Pd+2]
palladium hydroxide on carbon

Lösungsmittel

CCO
ethanol

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    FiltrationFilter
  2. 2
    Einengenconcentrate

Vorschrift

Add 20% palladium hydroxide on carbon (Pearlman's catalyst) (92 mg) to a solution of 5-(S)-benzyloxymethyl-2-(S)-(2-cyclohexylethyl)-morpholine-4-carboxylic acid tert-butyl ester (211 mg, 0.51 mmol) in absolute ethanol (25 mL) and hydrogenate in a Parr shaker at 40° C. for 18 hours at 60 psi. Filter and concentrate to give the desired compound which is used without further purification.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745438B2uspto-grants-2010_06