Diisobutylaluminum hydride → HCID 58700552, compound

HRID 517370Notes

Reaction equation

HRID 517370 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:16][C@@H:11]2[O:12][C:13](=[O:15])[CH2:14][C@@H:10]2[C@H:9]1/[CH:17]=[CH:18]/[C@@H:19]([O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=1.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]1[CH2:16][C@@H:11]2[O:12][CH:13]([OH:15])[CH2:14][C@@H:10]2[C@H:9]1/[CH:17]=[CH:18]/[C@@H:19]([O:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][O:34]1)[CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:29])([F:30])[F:31])[CH:23]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 117874872HCID 117874872, compound

Product 1

HCID 58700552HCID 58700552, compoundYield 130.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-70 °C

Procedure

(3aR,4R,5R,6aS)-5-((tetrahydro-2H-pyran-2-yl)oxy)-4-((3R,E)-3-((tetrahydro-2H-pyran-2-yl)oxy)-4-(3-(trifluoromethyl)phenoxy)but-1-en-1-yl)hexahydro-2H-cyclopenta[b]furan-2-one (19.0 g, 35.3 mmol) was dissolved in toluene (200 mL), followed by cooling to −70° C., and DIBAL (1.0M in hexane, 53 mL, 53 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 a 2M sodium bisulfate aqueous solution (200 mL) at room temperature and 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 25.0 g of crude titled 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 a 2M sodium bisulfate aqueous solution (200 mL) 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-57153dc46c514f20a3b754503ace30db
Source dataset
uspto-grants-2015_08
Patent number
US09115109B2

Reaction notes

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