Diisobutylaluminum hydride → HCID 117873536, compound
Reaction equation
[F:1][C:2]([F:29])([CH2:21][O:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][C:10](=[O:13])[CH2:11]2)[CH2:7][C@H:6]1[O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:29][C:2]([F:1])([CH2:21][O:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)/[CH:3]=[CH:4]/[C@@H:5]1[C@@H:12]2[C@@H:8]([O:9][CH:10]([OH:13])[CH2:11]2)[CH2:7][C@H:6]1[O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
(3aR,4R,5R,6aS)-4-((E)-3,3-difluoro-4-phenoxybut-1-enyl)-hexahydro-5-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]furan-2-one (47.0 g, 0.11 mol) was dissolved in toluene (500 mL), followed by cooling to −70° C., and DIBAL (1.0M in Hexane, 172 mL, 0.16 mol) was added dropwisely. Then the reaction was quenched by adding saturated aqueous solution of ammonium chloride (25 mL) at −70° C. The resulting mixture was poured into a 2M sodium bisulfate aqueous solution (500 mL) at room temperature and stirring was continued for 30 minutes. After separation of the organic layers, 500 mL of toluene was added to the aqueous layer. The combined organic layers were concentrated under reduced pressure to give 48 g of crude title compound.
Workup
- customThen the reaction was quenched
- additionby adding saturated aqueous solution of ammonium chloride (25 mL) at −70° C
- additionThe resulting mixture was poured into a 2M sodium bisulfate aqueous solution (500 mL) at room temperature
- customAfter separation of the organic layers, 500 mL of toluene
- additionwas added to the aqueous layer
- concentrationThe combined organic layers were concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-d371ff9bea604fd8896d850d0b3890c2
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09115109B2
Reaction notes
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