Benzyl Bromide → (3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-one

HRID 247704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247704
[H-].[Na+].C([N:10]1[C@H:13](CCO)[C@@H:12]([C@H:17]([O:19][Si:20]([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21])[CH3:18])[C:11]1=[O:27])C1C=CC=CC=1.C(Br)C1C=CC=CC=1>O.C1COCC1.CN(C)C=O>[Si:20]([O:19][C@@H:17]([C@@H:12]1[CH2:13][NH:10][C:11]1=[O:27])[CH3:18])([C:23]([CH3:26])([CH3:24])[CH3:25])([CH3:22])[CH3:21]

Komponenten

7

Edukt 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 139595691-benzyl-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-4(R)-(2-hydroxyethyl)-2-azetidinone

Produkt 1

HCID 10130795(3S)-3-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]azetidin-2-oneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

There were added 1 ml of THF and 0.6 ml of dimethylformamide to 13 mg (0.26 mmol) of sodium hydride (oiliness: 50%), to which 2 ml of a THF solution of 64 mg (0.18 mmol) of 1-benzyl-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-4(R)-(2-hydroxyethyl)-2-azetidinone on the ice bath and the mixture was stirred for 10 minutes. Thereto 0.03 ml (0.25 mmol) of benzyl bromide was added and the mixture was stirred at room temperature for a night. The reaction mixture was added with water, extracted three times with diethyl ether, and the obtained extract was washed with a saturated aqueous solution of sodium chloride, dried with anhydrous magnesium sulfate and concentrated. The obtained residue was purified by 10 g of silica gel-column chromatography (eluent; hexane:diethyl ether=1:1) to give 46 mg of 1-benzyl-4(R)-2-benzyloxyethyl)-3(S)-[1(R)-t-butyldimethylsilyloxyethyl]-2-azetidinone (yield: 58%).

Aufarbeitung

  1. extractionextracted three times with diethyl ether
  2. extractionthe obtained extract
  3. washwas washed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationconcentrated
  6. customThe obtained residue was purified by 10 g of silica gel-column chromatography (eluent; hexane:diethyl ether=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5529d26c64614193a5c8a7a4375d5f6c
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04709064

Notizen zur Reaktion

Wird geladen…