2-(Pyridin-3-yl)ethan-1-amine → {2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl}[2-(pyridin-3-yl)ethyl]amine

HRID 76227

Reaktionsgleichung

Reaktionsgleichung von HRID 76227
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@:7]1([CH2:17][CH:18]=O)[CH2:16][C:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.[N:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][CH2:27][NH2:28])[CH:21]=1.[BH4-].[Na+]>CO.C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@@:7]1([CH2:17][CH2:18][NH:28][CH2:27][CH2:26][C:22]2[CH:21]=[N:20][CH:25]=[CH:24][CH:23]=2)[CH2:16][C:11]2([CH2:15][CH2:14][CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 3

HCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 4311764Sodium borohydrideHCID 866714272-[(9R)-9-pyridin-2-yl-6-oxaspiro[4.5]decan-9-yl]acetaldehyde

Produkt 1

HCID 68314495{2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl}[2-(pyridin-3-yl)ethyl]amine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]acetaldehyde (50 mg, 0.19 mmole), 5 mL DCM and NA2SO4 (134 mg, 0.95 mmole) was added 2-(pyridin-3-yl)ethan-1-amine (31 mg, 0.25 mmole) and the reaction was stirred overnight. NaBH4 (9.5 mg, 0.25 mmole) added, stir 10 minutes, 2 drops MeOH added, stir 1 h, quenched with water, organics separated off and evaporated. The residue was passed through a Gilson reverse phase HPLC to give {2-[(9R)-9-(pyridin-2-yl)-6-oxaspiro[4.5]decan-9-yl]ethyl}[2-(pyridin-3-yl)ethyl]amine, 65.3 mg (71%). LCMS m/z 367.1 (M+1) observed.

Aufarbeitung

  1. stirringstir 10 minutes
  2. stirringstir 1 h
  3. customquenched with water
  4. customorganics separated off
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7e83c6038e084f6d92a93b7c8b081ab8
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835488B2

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