Methanol → HCID 20336554, compound

(Z)-3-Methoxycarbonylmethylene-4-oxa-1-azabicyclo[3.2.0]-heptan-7-one (120 mg., 0.65 mmole) was dissolved in dry 1,2-dimethoxyethane (5 ml.)/dry) toluene (5 ml.) and the solution was stirred at -30° under a dry nitrogen atmosphere while a 20% solution of di-isobutyl aluminium hydride in toluene (0.5 ml.) was added dropwise. After addition was complete, the mixture was stirred at -30° to -10° for 1 hour. Methanol (1 ml.) was added to the solution which was then diluted with ethyl acetate (30 ml). The solution was washed once with saturated brine to which a few drops of 2 N. HCl had been added. The solution was dried and the solvent was evaporated under reduced pressure to yield a yellow gum. The gum was chromatographed on silica gel (10 g.) using ethyl acetate/petroleum ether (b.p. 60°-80°) to give the title compound as a colourless oil (5 mg.). νmax (CHCl 3): 3350 (hydroxyl OH), 1793 (β-lactam C=O), 1695 (olefinic C=C)cm-1. δ (CDCl3): 2.95 (d, J 16 Hz, 1H, C(6)H), 3.38 (dd, J 16, J' 2 Hz, 1H, C(6)H). 3.56 (d, 17 Hz, 1H, C(2)H), 4.18 (d, 7 Hz, 2H, CH2O), 4.52 (d, J 17 Hz, 1H, C(2)H), 4.60 (t, J 7 Hz, 1H, olefinic H), 5.47 (d, J 2 Hz, 1H, C(5)H).

1. additionwas added dropwise
2. additionAfter addition
3. washThe solution was washed once with saturated brine to which a few drops of 2 N
4. additionHCl had been added
5. customThe solution was dried
6. customthe solvent was evaporated under reduced pressure
7. customto yield a yellow gum
8. customThe gum was chromatographed on silica gel (10 g.)

ORD record

ord-2a39bb4b7acf490a8218827939a8d386

Source dataset

uspto-grants-1980_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04206120