Aluminium lithium hydride → tert-Butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylate

HRID 1867598Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1867598
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([O:11][C:12]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][C:21]([NH:23][C@H:24]([C:44](O)=[O:45])[CH2:25][O:26][Si:27]([C:40]([CH3:43])([CH3:42])[CH3:41])([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:22])[CH2:16][CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8]>O1CCCC1>[Si:27]([O:26][CH2:25][CH:24]([NH:23][C:21]([NH:20][CH:17]1[CH2:16][CH2:15][N:14]([C:12]([O:11][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:13])[CH2:19][CH2:18]1)=[O:22])[CH2:44][OH:45])([C:40]([CH3:41])([CH3:42])[CH3:43])([C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 68825752N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-O-[tert-butyl(diphenyl)silyl]serine

Produkt 1

HCID 68568228tert-Butyl 4-[({[2-{[tert-butyl(diphenyl)silyl]oxy}-1-(hydroxymethyl)ethyl]amino}carbonyl)amino]piperidine-1-carboxylateAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Lithium aluminum hydride (1 M, 0.703 mL, 0.703 mmol) was added to a solution of N-({[1-(tert-butoxycarbonyl)piperidin-4-yl]amino}carbonyl)-O-[tert-butyl(diphenyl)silyl]serine (373 mg, 0.639 mmol) in tetrahydrofuran (20 mL) at −78° C. The reaction was quenched with saturated ammonium chloride solution and partitioned between dichloromethane and saturated sodium bicarbonate solution. The organic layer was dried over sodium sulfate, filtered, and concentrated. Purification by silica gel chromatography (1%→8% methanol {1% ammonium hydroxide}/dichloromethane) gave the title compound (100 mg). MS 556.3 (M+1)

Aufarbeitung

  1. customThe reaction was quenched with saturated ammonium chloride solution
  2. custompartitioned between dichloromethane and saturated sodium bicarbonate solution
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by silica gel chromatography (1%→8% methanol {1% ammonium hydroxide}/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-1664be202c574ce39031fc0b2645b5a9
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07632832B2

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