Diisobutylaluminum hydride → HCID 13046422, compound

HRID 517402Notes

Reaction equation

HRID 517402 reaction equation
[C:1]1([CH2:7][CH2:8][C@H:9]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)/[CH:10]=[CH:11]/[C@@H:12]2[C@@H:19]3[C@@H:15]([O:16][C:17](=[O:20])[CH2:18]3)[CH2:14][C@H:13]2[O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[C:1]1([CH2:7][CH2:8][C@H:9]([O:28][CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][O:30]2)/[CH:10]=[CH:11]/[C@@H:12]2[C@@H:19]3[C@@H:15]([O:16][CH:17]([OH:20])[CH2:18]3)[CH2:14][C@H:13]2[O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 11102745(3aR, 4R, 5R, 6aS) Hexahydro-4-[(E)-(3S)-5-phenyl-3-(tetrahydropyran-2-yloxy)-1-pentenyl]-5-(tetrahydropyran-2-yloxy)-2H-cyclopenta[b]furan-2-one

Product 1

HCID 13046422HCID 13046422, compoundYield 128%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-70 °C

Procedure

(3aR,4R,5R,6aS)-hexahydro-4-((S,E)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pent-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)cyclopenta[b]furan-2-one (14.0 g from Example 46) was dissolved in toluene (140 mL), followed by cooling to −70° C., and DIBAL (1.0M in Hexane, 45 mL) was added dropwisely. Then the reaction was quenched by adding saturated aqueous solution of ammonium chloride (10 mL) at −70° C. The resulting mixture was poured into 90 mL of a 2M sodium bisulfate aqueous solution at room temperature and stirring was continued for 30 minutes. After separation of the organic layers, 200 mL of toluene was added to the aqueous layer. The combined organic layers were concentrated under reduced pressure to give 18.0 g of crude title compound.

Workup

  1. customThen the reaction was quenched
  2. additionby adding saturated aqueous solution of ammonium chloride (10 mL) at −70° C
  3. additionThe resulting mixture was poured into 90 mL of a 2M sodium bisulfate aqueous solution at room temperature
  4. customAfter separation of the organic layers, 200 mL of toluene
  5. additionwas added to the aqueous layer
  6. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-0660fb2c37d64666bd666fcc87dce376
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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