Tetrabutylammonium Fluoride → (3aR,4S,5R,6aS)-4-(hydroxymethyl)-5-phenylmethoxy-3,3a,4,5,6,6a-hexahydrocyclopenta[b]furan-2-one
Reaction equation
C([Si](C(C)C)(C(C)C)[O:5][CH2:6][C@@H:7]1[C@@H:14]2[C@@H:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][C@H:8]1[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>O1CCCC1>[OH:5][CH2:6][C@@H:7]1[C@@H:14]2[C@@H:10]([O:11][C:12](=[O:15])[CH2:13]2)[CH2:9][C@H:8]1[O:16][CH2:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (3aR,4S,5R,6aS)-hexahydro-4-(triisopropylsilyloxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one (4, R1 is phenyl, R2 and R3 are H, and R8 is TIPS, 49 g, 0.117 mol) in tetrahydrofuran (7 vol) at 0° C. was added TBAF (128 mL, 0.129 mol) and the mixture was stirred for 2 h. After completion of the reaction, the reaction mixture was concentrated to dryness and purified by column chromatography [55% ethyl acetate in heptanes] to yield (3aR,4S,5R,6aS)-hexahydro-4-(hydroxymethyl)-5-(phenylmethoxy)-2H-cyclopenta[b]furan-2-one (5, R1 is phenyl, and R2 and R3 are H) in quantitative yield. 1H NMR (CDCl3): δ 2.12 (m, 3H), 2.53 (m, 2H), 2.74 (m, 2H), 3.51 (m, 2H), 3.89 (m, 1H), 4.48 (dd, J=47.9, 11.5 Hz, 2H), 4.92 (m, 1H), 7.27 (m, 5H).
Workup
- customAfter completion of the reaction
- concentrationthe reaction mixture was concentrated to dryness
- custompurified by column chromatography [55% ethyl acetate in heptanes]
Sources & evidence
- ORD record
- ord-4fdd3e8390e44837a1a8cd67c0a18e5b
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09382272B2
Reaction notes
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