2-Hydroxy-2-methyl-1-phenylpropan-1-one → 3-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile

HRID 133469

Reaktionsgleichung

Reaktionsgleichung von HRID 133469
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([C:19]#[N:20])[CH:14]=2)[C@@H:10]([NH2:12])[CH3:11])=[CH:4][CH:3]=1.[OH:21][C:22]([CH3:32])([CH3:31])[C:23]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([C:13]2[CH:14]=[C:15]([CH:16]=[CH:17][CH:18]=2)[C:19]#[N:20])[C@@H:10]([NH:12][CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([OH:21])([CH3:32])[CH3:31])[CH3:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 819842-Hydroxy-2-methyl-1-phenylpropan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 115872963-((2S,3S)-3-amino-1-(4-chlorophenyl)butan-2-yl)benzonitrile

Produkt 1

HCID 112126573-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 250 mg (0.877 mmol) of 3-(4-chlorophenyl)-2(S)(3-cyanophenyl)-1(S)-methyl-propylamine in 3 mL of dichloroethane, 134 μL (0.88 mmol) of 2-hydroxy-2-methylpropiophenone and 280 mg (1.32 mmol) of sodium triacetoxyborohydride were added. After stirring for 3 hr, the reaction was quenched with water and the organic layer was removed with a pipet. This layer was purified by prep TLC using 50% EtOAc/hexane as an eluant to isolate 3-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile (diastereomer A) as a higher Rf isomer (LC-MS: m/e=433 (M+1), 3.09 min) and 3-(1(S)-(4-Chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile (diastereomer B) as a lower Rf isomer. LC-MS: m/e=433 (M+1), 3.09 min.

Aufarbeitung

  1. customthe reaction was quenched with water
  2. customthe organic layer was removed with a pipet
  3. customThis layer was purified by prep TLC

Quellen und Nachweise

ORD-Eintrag
ord-d3fee5ce75254e2383ad83259607b2c4
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390835B2

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