Vinyl Acetate → (1S,3R)-2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione

HRID 2280725Notes

Reaction equation

HRID 2280725 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH2:5][CH:4]([N:8]2[C:16](=[O:17])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]2=[O:18])[CH2:3]1.C(OC(=O)C)=C>C1COCC1>[OH:1][C@@H:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([N:8]2[C:9](=[O:18])[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]2=[O:17])[CH2:3]1

Participants

4

Reactant 2

HCID 7904Vinyl AcetateHCID 41897092-(3-Hydroxycyclohexyl)isoindoline-1,3-dione

Product 1

HCID 69434411(1S,3R)-2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dioneYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione (240 g, 0.98 mol) and Lipase B (87 g) in THF (3000 mL) was stirred at room temperature under nitrogen for 1˜2 h. Then acetic acid vinyl ester (252 g, 2.88 mol) was added to the solution, and the reaction mixture was stirred at rt for 3˜5 h. Then the reaction mixture was filtered, and the filtrate was concentrated to give crude product. The crude product was purified on silica gel (eluting with petroleum ether/ethyl acetate=10:1) to give (1S,3R)-2-(3-hydroxy-cyclohexyl)-isoindole-1,3-dione (Rf=0.6, petroleum ether/ethyl acetate=3/1, 90 g, 0.37 mol, yield: 39%) as a white solid. 1H NMR (CD3OD, 400 MHz): δ ppm 7.82 (m, 4H), 4.16 (m, 1H), 3.63 (m, 1H), 2.13 (m, 2H), 1.98 (m, 2H), 1.89 (m, 1H), 1.68 (m, 1H), 1.46 (m, 1H), 1.31 (m, 1H).

Workup

  1. filtrationThen the reaction mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. customto give crude product
  4. customThe crude product was purified on silica gel (eluting with petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-c6519effa305429c9dd6b3cfafb9f989
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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