Toluene → N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)amino]-1-phenyl-ethyl]carbamic acid tert-butyl ester

HRID 32462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32462
[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:9]([NH:11][CH2:12][CH:13]1[CH2:18][CH2:17][N:16]([CH:19]([CH3:21])[CH3:20])[CH2:15][CH2:14]1)=O)([CH3:4])([CH3:3])[CH3:2].[H-].COCCO[Al+]OCCOC.[Na+].[H-].C1(C)C=CC=CC=1>C1COCC1>[C:1]([O:5][C:6](=[O:28])[NH:7][C@H:8]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:9][NH:11][CH2:12][CH:13]1[CH2:14][CH2:15][N:16]([CH:19]([CH3:20])[CH3:21])[CH2:17][CH2:18]1)([CH3:3])([CH3:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 69308038N-[(R)-2-[(1-isopropylpiperidin-4-yl-methyl) amino]-1-phenyl-2-oxoethyl]carbamic acid tert-butyl ester

Produkt 1

HCID 69307988N-[(R)-2-[(1-Isopropylpiperidin-4-ylmethyl)amino]-1-phenyl-ethyl]carbamic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-[(R)-2-[(1-isopropylpiperidin-4-yl-methyl) amino]-1-phenyl-2-oxoethyl]carbamic acid tert-butyl ester (1.0 g, 2.6 mmol) in 15 mL of THF was added 65 wt % sodium bis(2-methoxyethoxy)aluminum hydride in toluene (2.4 mL, 7.7 mmol). The reaction mixture was heated at reflux for 3 h after which time the mixture was cooled to 0° C. and the reaction was quenched by the slow addition of a saturated solution of Rochelle's salt. The product was extracted into EtOAc; and the combined extracts were dried over sodium sulfate, filtered, and concentrated to afford, after purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 0.9 g (94%) of the title compound.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 3 h after which time the mixture
  3. customthe reaction was quenched by the slow addition of a saturated solution of Rochelle's salt
  4. extractionThe product was extracted into EtOAc
  5. dry with materialand the combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford
  9. customafter purification (SiO2: 0 to 30% isopropylamine in 1:1 hexane:EtOAc), 0.9 g (94%) of the title compound

Quellen und Nachweise

ORD-Eintrag
ord-ebaf8ec6a282496199629941bb97c380
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427632B2

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