HCID 68772872, compound → HCID 86648187, compound

HRID 2191380Notes

Reaction equation

HRID 2191380 reaction equation
[CH3:1][C:2]1([CH3:33])[O:6][C@@H:5]2[C:7]([CH2:12][O:13][C:14](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:8][C@@H:9](C=C)[C@@H:4]2[O:3]1>CC1(C)OO1.CC(C)=O>[CH3:33][C:2]1([CH3:1])[O:3][C@@H:4]2[CH:9]=[CH:8][C@@H:7]([C@H:12]3[CH2:14][O:13]3)[C@@H:5]2[O:6]1

Participants

4

Reactant 1

HCID 68772872HCID 68772872, compound

Product 1

HCID 86648187HCID 86648187, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 115197DimethyldioxiraneSolvent

Conditions

Temperature
-20 °C

Procedure

(3aS,4R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-4-vinyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (2-3) (7.0 g, 42.1 mmol, 1.0 equiv) was dissolved in a freshly prepared solution of DMDO in acetone (460 mL, 0.085 M, 0.9 equity), stirred at −20° C. for 7 hours and stored at −18° C. overnight. The reaction mixture was concentrated and purified via flash chromatography on a silica gel column (ethyl acetate/hexanes) to yield desired (3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (2-4) as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 5.92 (t, J=5.7 Hz, 1H); 5.75-5.71 (m, 1H); 5.17 (d, J=5.8 Hz, 1H); 4.70-4.57 (m, 1H); 2.98-2.89 (m, 2H); 2.77-2.72 (m, 1H); 2.55 (dt, J=4.8, 2.8 Hz, 1H); 1.41 (s, 3H); 1.35 (d, J=2.3 Hz, 3H).

Workup

  1. waitstored at −18° C. overnight
  2. concentrationThe reaction mixture was concentrated
  3. custompurified via flash chromatography on a silica gel column (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5bca38b2d62d4ce4b36e26ca72828037
Source dataset
uspto-grants-2012_12
Patent number
US08329697B2

Reaction notes

Loading…