Sodium cyanoborohydride → ((1R)-1-Phenylpropyl){[4-methoxy-3-(4-methoxyphenyl)phenyl]methyl}amine

HRID 1072251

Reaktionsgleichung

Reaktionsgleichung von HRID 1072251
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:7][C:6]([CH2:17][NH:18][CH:19]([C:21]2C3C(=CC=CC=3)N=C[CH:22]=2)C)=[CH:5][CH:4]=1.[C:31]1([C@H](N)CC)[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.COC1C(C2C=CC(OC)=CC=2)=CC(C=O)=CC=1.C([BH3-])#N.[Na+]>>[C:31]1([C@H:19]([NH:18][CH2:17][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[C:8]([C:9]3[CH:10]=[CH:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=3)[CH:7]=2)[CH2:21][CH3:22])[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Komponenten

5

Edukt 4

HCID 5003444Sodium cyanoborohydrideHCID 5324978(R)-1-PhenylpropylamineHCID 223911916,4'-Dimethoxybiphenyl-3-carbaldehydeHCID 22391337(6,4'-Dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine

Produkt 1

HCID 60010370((1R)-1-Phenylpropyl){[4-methoxy-3-(4-methoxyphenyl)phenyl]methyl}amineAusbeute 52 %

Versuchsvorschrift

The title compound was prepared by the same procedure for (6,4′-dimethoxybiphenyl-3-ylmethyl)-(1-quinolin-4-yl-ethyl)-amine from (R)-(+)-1-phenyl-propylamine (405 mg, 3.0 mmol, Lancaster Synthesis Ltd.), 6,4′-Dimethoxybiphenyl-3-carbaldehyde (242 mg, 1.0 mmol) and sodium cyanoborohydride (1.0 g, 16 mmol, Aldrich). The title compound was purified by column chromatography (silica gel, hexane/ethyl acetate 2/3) in form as white solid in 52% yield (187 mg, 0.52 mmol).

Aufarbeitung

  1. customThe title compound was purified by column chromatography (silica gel, hexane/ethyl acetate 2/3) in form as white solid in 52% yield (187 mg, 0.52 mmol)

Quellen und Nachweise

ORD-Eintrag
ord-0d8dcad1acff443f9496fd5fbb464e52
Quelldatensatz
uspto-grants-2005_06
Patentnummer
US06908935B2

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