Sodium borohydride → (3R,4R)-4-(2-hydroxyethyl)-3-phthalimidoazetidin-2-one

HRID 851396Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 851396
[O:1]=[CH:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@@H:5]1[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].[BH4-].[Na+]>CO.ClCCl>[OH:1][CH2:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@@H:5]1[N:9]1[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]2[C:13]1=[O:14]

Komponenten

5

Edukt 2

HCID 4311764Sodium borohydrideHCID 53769960(3R,4R)-4-(2-oxoethyl)-3-phthalimido-2-oxoazetidine

Produkt 1

HCID 53834571(3R,4R)-4-(2-hydroxyethyl)-3-phthalimidoazetidin-2-oneAusbeute 51,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (3R,4R)-4-(2-oxoethyl)-3-phthalimidoazetidin-2-one (52 mg) in a mixture of methanol (3 ml) and dichloromethane (1 ml) was added a solution of sodium borohydride (8 mg) in methanol (2 ml) at 0° C. during one hour. The reaction was quenched by addition of acetic acid (two drops). After evaporation in vacuo, the residue was chromatographed on silica gel (1.6 g; eluting with 3 to 5% methanol in dichloromethane) to give 32 mg of crude crystals. Crystallization from a mixture of methanol and ether afforded 27 mg (51.5%) of (3R,4R)-4-(2-hydroxyethyl)-3-phthalimidoazetidin-2-one. IR (Nujol): 3350(br), 3250, 1750, and 1705 cm-1 ; NMR (DMSO-d6) δ: 1.79 (q, J=6 Hz, 2H), 3.46 (m, 2H), 3.97 (dt, J=2.5 and 6 Hz, 1H), 4.47 (brs, 1H), 4.89 (d, J=2.5 Hz, 1H), 7.86 (s, 4H), and 8.42 (brs, 1H).

Aufarbeitung

  1. customThe reaction was quenched by addition of acetic acid (two drops)
  2. customAfter evaporation in vacuo
  3. customthe residue was chromatographed on silica gel (1.6 g; eluting with 3 to 5% methanol in dichloromethane)
  4. customto give 32 mg of crude crystals
  5. customCrystallization
  6. additionfrom a mixture of methanol and ether

Quellen und Nachweise

ORD-Eintrag
ord-722e2a9a247049278f71fff9fff0b43f
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04383945

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