Ozone → 3-Benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester

HRID 1912391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912391
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])([CH:14]([CH3:17])[CH:15]=C)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O:29]=[O+][O-].[BH4-].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([NH:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])([CH:14]([CH3:17])[CH2:15][OH:29])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 24823OzoneHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 582933873-Benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid tert-butyl ester

Produkt 1

HCID 582933703-Benzyloxycarbonylamino-3-(2-hydroxy-1-methylethyl)piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21584188Chloroform methanolLösungsmittel

Versuchsvorschrift

A solution of an optically-active compound of 3-benzyloxycarbonylamino-3-(1-methylallyl)piperidine-1-carboxylic acid 1-tert-butyl ester (815 mg) in chloroform/methanol (6.6 ml/6.6 ml) cooled to −78° C. was flowed ozone air for 30 minutes. To the reaction mixture was added sodium borohydride (318 mg) in small batches, and then the mixture was warmed to room temperature over 40 minutes. To the mixture was added saturated aqueous sodium bicarbonate solution, and the mixture was extracted with chloroform twice. The combined organic layer was washed with aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/2 to 0/1) to give the titled compound (406 mg).

Aufarbeitung

  1. customfor 30 minutes
  2. extractionthe mixture was extracted with chloroform twice
  3. washThe combined organic layer was washed with aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=3/2 to 0/1)

Quellen und Nachweise

ORD-Eintrag
ord-e048bfe1d4944b3eb3f4b092f1d50a53
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609647B2

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