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

HRID 133471Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133471
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20]#[N:21])[CH:15]=2)[C@@H:11]([NH2:13])[CH3:12])=[CH:5][CH:4]=1.C(N(C(C)C)CC)(C)C.Cl[C:32]1[CH:37]=[CH:36][C:35]([C:38](=O)[C:39]([CH3:42])([OH:41])[CH3:40])=[CH:34][CH:33]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C@@H:10]([C:14]2[CH:15]=[C:16]([CH:17]=[CH:18][CH:19]=2)[C:20]#[N:21])[C@@H:11]([NH:13][CH:38]([C:35]2[CH:36]=[CH:37][CH:32]=[CH:33][CH:34]=2)[C:39]([OH:41])([CH3:42])[CH3:40])[CH3:12])=[CH:5][CH:4]=1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 144194521-(4-Chlorophenyl)-2-methyl-2-hydroxy-propan-1-oneHCID 692680263-((2S,3S)-3-Amino-1-(4-chlorophenyl)butan-2-yl)benzonitrile hydrochloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 100 mg (0.31 mmol) of 3-(4-chlorophenyl)-2(S)-(3-cyanophenyl)-1(S)-methyl-propylamine hydrochloride in 2 mL of CH2Cl2, 54 μL (0.31 mmol) of diisopropylethylamine and 62 mg (0.31 mmol) of 1-(4-chlorophenyl)-2-methyl-2-hydroxy-propan-1-one were added. After 5 min, 99 mg (0.47 mmol) of sodium triacetoxyborohydride was added and stirred for 3 hr. The reaction was quenched with water and the layers were separated. The organic layer was dried and concentrated. The residue was purified on a prep TLC plate using 30% EtOAc/hexane as an eluant to isolate two products. The higher Rf band gave 3-(1(S)-(4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile (diastereomer A) and the lower Rf band gave 3-(1(S)-4-chlorobenzyl)-2(S)-((2-hydroxy-2-methyl-1-phenylpropyl)amino)propyl)benzonitrile (diastereomer B). Diastereomer A, LC-MS: m/e=467 (M+1), 469 (M+3) (3.28 min). Diastereomer B, LC-MS: m/e=467 (M+1), 469 (M+3) (3.28 min).

Aufarbeitung

  1. customThe reaction was quenched with water
  2. customthe layers were separated
  3. customThe organic layer was dried
  4. concentrationconcentrated
  5. customThe residue was purified on a prep TLC plate
  6. customto isolate two products

Quellen und Nachweise

ORD-Eintrag
ord-b26a987bcd5f4f39be867e0537a4e429
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390835B2

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