Reaktion #71618

ord-d3f1cc6cc426466f9662703f3e0ae627

Reaktionsgleichung

O=C([O-])O.[Na+]
NaHCO3
O=Cc1ccc(Br)cc1
4-bromobenzaldehyde
C[C@H]1CNCCN1C(=O)OCc1ccccc1
phenylmethyl (2S)-2-methyl-1-piperazinecarboxylate
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride
→
C[C@H]1CN(Cc2ccc(Br)cc2)CCN1C(=O)OCc1ccccc1
title compound
Ausbeute 84.2%
C[C@H]1CN(Cc2ccc(Br)cc2)CCN1C(=O)OCc1ccccc1
Phenylmethyl (2S)-4-[(4-bromophenyl)methyl]-2-methyl-1-piperazine Carboxylate
Ausbeute 84.2%

Edukte

O=C([O-])O.[Na+]
NaHCO3
O=Cc1ccc(Br)cc1
4-bromobenzaldehyde
C[C@H]1CNCCN1C(=O)OCc1ccccc1
phenylmethyl (2S)-2-methyl-1-piperazinecarboxylate
CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
sodium triacetoxyborohydride

Reagenzien

Keine

Lösungsmittel

ClCCCl
1,2-DCE

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.STIRRINGthe mixture stirred for 30 mins
  2. 2
    ExtraktionProduct was extracted
  3. 3
    Trocknenthe extracts dried (Na2SO4)

Vorschrift

A mixture of 4-bromobenzaldehyde (1.19 g, 6.42 mmol), phenylmethyl (2S)-2-methyl-1-piperazinecarboxylate (1.505 g, 6.42 mmol) and sodium triacetoxyborohydride (2.04 g, 9.63 mmol) in 1,2-DCE (15 ml) was stirred at room temperature overnight. Saturated aq. NaHCO3 solution was added and the mixture stirred for 30 mins. Product was extracted and the extracts dried (Na2SO4). Chromatography (0-30% EtOAc in pentane) gave the title compound (2.18 g). MS (ES): MH+ 403/405.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536182B2uspto-grants-2013_09