4-Bromobenzaldehyde → Phenylmethyl (2S)-4-[(4-bromophenyl)methyl]-2-methyl-1-piperazine Carboxylate

HRID 43340

Reaktionsgleichung

Reaktionsgleichung von HRID 43340
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][C@H:11]1[CH2:16][NH:15][CH2:14][CH2:13][N:12]1[C:17]([O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:18].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH2:6][N:15]2[CH2:14][CH2:13][N:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C@@H:11]([CH3:10])[CH2:16]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 707414-BromobenzaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 40425199Benzyl (2S)-2-methylpiperazine-1-carboxylate

Produkt 1

HCID 25224210Phenylmethyl (2S)-4-[(4-bromophenyl)methyl]-2-methyl-1-piperazine CarboxylateAusbeute 84,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. stirringthe mixture stirred for 30 mins
  2. extractionProduct was extracted
  3. dry with materialthe extracts dried (Na2SO4)

Quellen und Nachweise

ORD-Eintrag
ord-d3f1cc6cc426466f9662703f3e0ae627
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536182B2

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