Dimethyl Sulfide → (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate

HRID 218398Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 218398
S(C)C.C1(C)C=CC=CC=1.[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:33])=[C:16]([CH:32]=1)[C:17]([C@@H:19]1[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:20]1)=[O:18]>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:33])=[C:16]([C@H:17]([OH:18])[C@@H:19]2[CH2:24][CH2:23][CH2:22][N:21]([C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[CH2:20]2)[CH:32]=1

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 1140TolueneHCID 58011514(R)-tert-butyl 3-(5-chloro-2-methylbenzoyl)piperidine-1-carboxylate

Produkt 1

HCID 58011541(R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

A mixture of 10 M BH3.Me2S in THF (25.4 mL, 0.254 mol) and 1 M R-CBS-oxazaborolidine in toluene (38 mL, 0.038 mol) were dissolved in 100 mL anhydrous THF and cooled to −15° C. (R)-tert-butyl 3-(5-chloro-2-methylbenzoyl)piperidine-1-carboxylate in 200 mL anhydrous THF was added dropwise to the above solution and stirred at −15° C. for 2 hr. The reaction was quenched with methanol (300 mL). The solvent was removed under reduced pressure, and the residue was purified by column chromatography to give (R)-tert-butyl 3-((R)-(5-chloro-2-methylphenyl)(hydroxy)methyl)piperidine-1-carboxylate (32 g), which contained 30% isomer.

Aufarbeitung

  1. additionwas added dropwise to the above solution
  2. customThe reaction was quenched with methanol (300 mL)
  3. customThe solvent was removed under reduced pressure
  4. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-12eca16fba564987b6a4d6df7df18140
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08198453B2

Notizen zur Reaktion

Wird geladen…