Acetone → HCID 86648184, compound

HRID 2191372Notes

Reaction equation

HRID 2191372 reaction equation
[CH3:1][C:2]1([CH3:33])[O:6][C@@H:5]2[C:7]([CH2:12][O:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:8][C@@H:9]([CH:10]=[CH2:11])[C@@H:4]2[O:3]1.CC(C)=[O:36]>CC1(C)OO1>[CH3:1][C:2]1([CH3:33])[O:6][C@@H:5]2[C:7]([CH2:12][O:13][C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:8][C@@H:9]([C@H:10]3[CH2:11][O:36]3)[C@@H:4]2[O:3]1

Participants

4

Reactant 2

HCID 180AcetoneHCID 68772872HCID 68772872, compound

Product 1

HCID 86648184HCID 86648184, compound

Reagents, catalysts & solvents 1

HCID 115197DimethyldioxiraneSolvent

Conditions

Temperature
0 °C

Procedure

(3aS,4R,6aR)-2,2-dimethyl-6-(trityl oxymethyl)-4-vinyl-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-3) (1.4 g, 3.19 mmol, 1.0 equiv) was dissolved in a freshly prepared solution of DMDO (dimethyl dioxirane) in acetone (37.7 mL, 0.076 M, 0.9 equiv). The resulting mixture was stirred at 0° C. for 4 hours, then concentrated and purified via flash chromatography on silica gel column (ethyl acetate/hexanes) to yield (3aS,4S,6aR)-2,2-dimethyl-4-((S)-oxiran-2-yl)-6-(trityloxymethyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole (1-5). 1H NMR (500 MHz, CDCl3) δ 7.21-7.47 (m, 15H), 5.83 (2 s, 1H), 4.99 (t, 1H, J=5 Hz), 4.63 (t, 1H, J=5 Hz), 3.86 (d, 1H, J=14 Hz), 3.67 (d, 1H, J=14 Hz), 2.85-2.97 (m, 2H), 2.77 (m, 1H), 2.60 (m, 1H), 1.35 (s, 3H), 1.32 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompurified via flash chromatography on silica gel column (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-9d31dc14270446b98cc3868c5a0a2ad5
Source dataset
uspto-grants-2012_12
Patent number
US08329697B2

Reaction notes

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