Hydrochloric Acid → 2-hydroxysorbinil

HRID 482695Notes

Reaction equation

[F:1][C:2]1[CH:3]=[C:4]2[C:11]3([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]3)[CH2:10][C:9](=[O:18])[O:8][C:5]2=[CH:6][CH:7]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C.Cl>CCCCCC.O1CCCC1>[OH:18][CH:9]1[CH2:10][C:11]2([C:15](=[O:16])[NH:14][C:13](=[O:17])[NH:12]2)[C:4]2[C:5](=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=2)[O:8]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a slurry of 640 mg. (0.002 mole) of 6-fluorospiro[chroman-4,4'-imidazolidine]2,2',5'-trione in 40 ml. of toluene at -78° C. was added 852 mg. (0.006 mole) of diisobutylaluminum hydride in hexane, and the reaction mixture allowed to stir at -78° C. for 30 minutes. The reaction was allowed to warm to 0° C. and was stirred for 24 hours. The reaction was recooled to -40° C., 6 ml. of dry tetrahydrofuran was added and the reaction warmed to 0° C. Additional diisobutylaluminum hydride (1.0 ml) was added in 0.2 ml. portions. The reaction mixture was added to 10% hydrochloric acid and the mixture extracted with ethyl acetate. The combined extracts were washed dried and concentrated to dryness. The residue was chromatographed to give 67 mg. of the desired compound, m.p. 247°-251° C. (dec.).

Workup

temperatureto warm to 0° C.
stirringwas stirred for 24 hours
customwas recooled to -40° C.
temperaturethe reaction warmed to 0° C
extractionthe mixture extracted with ethyl acetate
washThe combined extracts were washed
customdried
concentrationconcentrated to dryness
customThe residue was chromatographed
customto give 67 mg

Sources & evidence

ORD record: ord-47492f45226e4e0891b1e34bdb9d9c49
Source dataset: uspto-grants-1986_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04575507

Reaction notes

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