Diisobutylaluminum hydride → HCID 42604333, compound

HRID 517386Notes

Reaction equation

HRID 517386 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)[CH2:10][CH2:11][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)[CH2:10][CH2:11][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 11102783HCID 11102783, compound

Product 1

HCID 42604333HCID 42604333, compoundYield 135.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-70 °C

Procedure

(3aR,4R,5R,6aS)-4-((3R)-5-phenyl-3-((tetrahydro-2H-pyran-2-yl)oxy)pentyl)-5-((tetrahydro-2H-pyran-2-yl)oxy)hexahydro-2H-cyclopenta[b]furan-2-one (22.0 g, 46.6 mmol) was dissolved in toluene (200 mL), followed by cooling to −70° C., and DIBAL (1.0M in hexane, 60 mL, 60.0 mmol) 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 200 mL of a 2M sodium bisulfate aqueous solution at room temperature and the stirring was continued for 30 minutes. After separation of the organic layers, toluene (200 mL) was added to the aqueous layer. The combined organic layers were concentrated under reduced pressure to give 30.0 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 200 mL of a 2M sodium bisulfate aqueous solution at room temperature
  4. customAfter separation of the organic layers, toluene (200 mL)
  5. additionwas added to the aqueous layer
  6. concentrationThe combined organic layers were concentrated under reduced pressure

Sources & evidence

ORD record
ord-db97ca45b2094f829f881611e1579ed0
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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