Reaktion #2018541

ord-8af2b62ff52346669aa1c8fc643de893

Reaktionsgleichung

O=C([O-])O.[Na+]
NaHCO3
C[C@H]1CCCN(C(=O)NC2C3CC4CC2CC(O)(C4)C3)C1
(S)-3-Methyl-piperidine-1-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide
CC(=O)Cl
acetyl chloride
c1ccncc1
pyridine
→
CC(=O)OC12CC3CC(C1)C(NC(=O)N1CCC[C@H](C)C1)C(C3)C2
title compound
CC(=O)OC12CC3CC(C1)C(NC(=O)N1CCC[C@H](C)C1)C(C3)C2
Acetic acid 4-[((S)-3-methyl-piperidine-1-carbonyl)-amino]-adamantan-1-yl ester

Edukte

O=C([O-])O.[Na+]
NaHCO3
C[C@H]1CCCN(C(=O)NC2C3CC4CC2CC(O)(C4)C3)C1
(S)-3-Methyl-piperidine-1-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide
CC(=O)Cl
acetyl chloride
c1ccncc1
pyridine

Reagenzien

Keine

Lösungsmittel

ClCCl
methylene chloride

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Extraktionthe organic phase extracted with methylene chloride
  2. 2
    Waschenwashed with HCl 1 N solution
  3. 3
    Trocknendried over sodium sulphate

Vorschrift

A mixture of (S)-3-Methyl-piperidine-1-carboxylic acid (5-hydroxy-adamantan-2-yl)-amide 0.15 g (0.51 mmol), 0.109 ml of acetyl chloride, 0.3 ml of pyridine in 1.5 ml of methylene chloride was stirred at room temperature overnight. A saturated NaHCO3 solution was added, the organic phase extracted with methylene chloride, washed with HCl 1 N solution and dried over sodium sulphate. Flash chromatography on silica gel (eluant CH2Cl2/MeOH: 95/05) yielded 75 mg of the title compound

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08188288B2uspto-grants-2012_05