Acetaldehyde → rac-[(3R,4S)-3-(3,4-Dichloro-phenyl)-4-ethylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

HRID 527473Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527473
[NH2:1][CH:2]1[CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([Cl:14])[CH:8]=2)[CH2:5][N:4]([C:15]([CH:17]2[CH2:22][CH2:21][N:20]([C:23]([C:25]3([CH3:28])[CH2:27][CH2:26]3)=[O:24])[CH2:19][CH2:18]2)=[O:16])[CH2:3]1.[CH:29](=O)[CH3:30].C([BH3-])#N.[Na+]>C(O)C>[Cl:14][C:9]1[CH:8]=[C:7]([C@H:6]2[C@H:2]([NH:1][CH2:29][CH3:30])[CH2:3][N:4]([C:15]([CH:17]3[CH2:22][CH2:21][N:20]([C:23]([C:25]4([CH3:28])[CH2:27][CH2:26]4)=[O:24])[CH2:19][CH2:18]3)=[O:16])[CH2:5]2)[CH:12]=[CH:11][C:10]=1[Cl:13]

Komponenten

5

Edukt 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 67238593rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone

Produkt 1

HCID 67237915rac-[(3R,4S)-3-(3,4-Dichloro-phenyl)-4-ethylamino-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanoneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of rac-(3S,4R)-[3-Amino-4-(3,4-dichloro-phenyl)-pyrrolidin-1-yl]-[1-(1-methyl-cyclopropanecarbonyl)-piperidin-4-yl]-methanone (50 mg, 0.12 mmol) in ethanol (0.3 mL) were added acetaldehyde (10 uL, 0.18 mmol) and sodiumcyanoborohydride (15 mg, 0.24 mmol) and the reaction mixture was stirred at ambient temperature for 3 h. It was concentrated and the residue separated between water and ethylacetate. The organic layer was dried over sodium sulfate and concentrated. Purification by chromatography (SiO2, dichloromethane:methanol=100:0 to 95:5) afforded the title compound (30 mg, 56%) as a light yellow oil. MS m/e: 452.3 [M]+.

Aufarbeitung

  1. concentrationIt was concentrated
  2. customthe residue separated between water and ethylacetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by chromatography (SiO2, dichloromethane:methanol=100:0 to 95:5)

Quellen und Nachweise

ORD-Eintrag
ord-b726b62f1cf84a4090fb11197ce01823
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346786B2

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