(1R,4S)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol → (1R,4R)-4-((tert-Butyldimethylsilyl)oxy)cyclopent-2-en-1-ol
Reaction equation
[OH:1][C@H:2]1[CH:6]=[CH:5][C@@H:4]([O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])[CH2:3]1>CCOC(C)=O.CCCCCC>[O:7]([C@H:4]1[CH:5]=[CH:6][C@H:2]([OH:1])[CH2:3]1)[Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
Compound 14 was subjected to general procedure J. Yield=81%. TLC: Rf=0.50 (10% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 2.20 (m, 1H), 2.30 (m, 1H), 5.10 (s, 1H), 6.05 (m, 2H), 6.10 (m, 1H), 8.20 (d, 2H), 8.20 (d, 2H). Subsequent subjection of the product to general procedure E gave compound 22. Yield=85%. TLC: Rf=0.33 (25% EtOAc/Hexane). 1H NMR (400 MHz, CDCl3): δ0.05 (s, 6H), 0.90 (s, 9H), 2.05 (m, 2H), 5.00 (m, 1H), 5.05 (m, 1H), 5.95 (m, 2H).
Sources & evidence
- ORD record
- ord-ada8f3ba0ee247e8815f310e840cabe8
- Source dataset
- uspto-grants-2005_05
- Patent number
- US06887880B2
Reaction notes
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