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Sodium Hydroxide → (2S,3S)-3-(5-(1-Cyanocyclopropyl)-2-methoxybenzyl)amino-2-phenylpiperidine

HRID 481486
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 481486
Cl.Cl.[C:3]1([C@H:9]2[C@@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:16]([C:18]1([C:21]2[CH:22]=[CH:23][C:24]([O:29][CH3:30])=[C:25]([CH:28]=2)[CH:26]=O)[CH2:20][CH2:19]1)#[N:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[C:16]([C:18]1([C:21]2[CH:22]=[CH:23][C:24]([O:29][CH3:30])=[C:25]([CH:28]=2)[CH2:26][NH:15][C@H:14]2[CH2:13][CH2:12][CH2:11][NH:10][C@H:9]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:20][CH2:19]1)#[N:17]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 190664325-(1-Cyanocyclopropyl)-2-methoxybenzaldehydeHCID 69654807(2S,3S)-2-Phenylpiperidin-3-amine dihydrochloride

Produkt 1

HCID 9799042(2S,3S)-3-(5-(1-Cyanocyclopropyl)-2-methoxybenzyl)amino-2-phenylpiperidineAusbeute 41 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of Compound 3 (150 mg, 0.60 mmol) and Compound 2 (145 mg, 0.72 mmol) in dry CH2Cl2 (5 ml) was added NaBH(OAc)3 (358 mg, 1.68 mmol) portionwise at room temperature. The reaction mixture was stirred at room temperature for 6 h. The mixture was basified to pH10-11 with 10% NaOH aq. with ice-cooling. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product. The crude product (300 mg) was purified by column chromatography on silica gel with CH2Cl2 -MeOH (20:1-10:1) to give Compound 4 (89 mg, 41%) as a yellow viscous oil.

Aufarbeitung

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give crude product
  8. customThe crude product (300 mg) was purified by column chromatography on silica gel with CH2Cl2 -MeOH (20:1-10:1)

Quellen und Nachweise

ORD-Eintrag
ord-eb5d9595d0754a179895ec8f0191ad83
Quelldatensatz
uspto-grants-1998_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05789423

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