(+/-)-(2R,3R)-1-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)-methyl]piperidine → (+/-)-(2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)methyl]piperidine

HRID 751163Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751163
C(OC([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[C@H:9]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[C:25]=1[CH3:33])=O)(C)(C)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Si:15]([O:14][C@@H:10]1[CH2:11][CH2:12][CH2:13][NH:8][C@H:9]1[CH2:22][NH:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[C:26]([Cl:32])[C:25]=1[CH3:33])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17]

Komponenten

3

Edukt 1

HCID 59754257(+/-)-(2R,3R)-1-tert-Butyloxycarbonyl-3-(tert-butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)-methyl]piperidine

Produkt 1

HCID 68459464(+/-)-(2S,3R)-3-(tert-Butyldimethylsilanyloxy)-2-[(3-chloro-4-cyano-2-methylphenylamino)methyl]piperidineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863450Trifluoroacetic acid methylene chlorideLösungsmittel

Versuchsvorschrift

A solution of 77G (170mg, 0.34 mmol) in 5% TFA/DCM (5 mL) was stirred at rt for 5 h and LC-MS showed completion. The mixture was concentrated and the residue was dissolved in EtOAc (30 mL), washed with saturated sodium bicarbonate solution (15 mL), brine (10 mL), dried (MgSO4) and evaporated to give desired product 77H (121 m, 89%) as a white solid: Rf (10% MeOH/DCM) 0.39; HPLC (Phenomenex Luna 5 u C18 4.6×50 mm, linear gradient over 4 min) retention time 3.2 min (100%); MS (ES) m/z 344.1 [M+H]+; HRMS calcd for C20H33N3OSiCl 394.2081, Found 394.2080.

Aufarbeitung

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in EtOAc (30 mL)
  3. washwashed with saturated sodium bicarbonate solution (15 mL), brine (10 mL)
  4. dry with materialdried (MgSO4)
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-7b49f91917884176803033b56604fefe
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

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