Diisobutylaluminum hydride → HCID 57857033, compound

HRID 561753Notes

Reaction equation

HRID 561753 reaction equation
[S:1]1[C:5]([C@H:6]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)/[CH:7]=[CH:8]/[C@@H:9]2[C@@H:16]3[C@@H:12]([O:13][C:14](=[O:17])[CH2:15]3)[CH2:11][C@H:10]2[O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:4][C:3]2[CH:32]=[CH:33][CH:34]=[CH:35][C:2]1=2.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[S:1]1[C:5]([C@H:6]([O:25][CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][O:27]2)/[CH:7]=[CH:8]/[C@@H:9]2[C@@H:16]3[C@@H:12]([O:13][CH:14]([OH:17])[CH2:15]3)[CH2:11][C@H:10]2[O:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][O:20]2)=[CH:4][C:3]2[CH:32]=[CH:33][CH:34]=[CH:35][C:2]1=2

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 57857038HCID 57857038, compound2×

Product 1

HCID 57857033HCID 57857033, compoundYield 112%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
10 °C

Procedure

To a cold (−65 to −75° C.) solution consisting of (3aR,4R,5R,6aS)-4-((3R,E)-3-(benzo[b]thiophen-2-yl)-3-(tetrahydro-2H-pyran-2-yloxy)prop-1-enyl)-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2H-cyclopenta[b]furan-2-one (intermediate 30, 0.369 mg, 0.740 mmol) in toluene (8 mL) was added a solution consisting of DIBAL-H in toluene (1 M, 1.11 mL) over the course of ten seconds. The reaction mixture was stirred for two hours and was complete as judged by TLC. The reaction mixture was warmed to 10° C. and was subsequently quenched with a 7:1 mixture of THF-water (8 mL). The reaction mixture was allowed to stir overnight (18 hours). After stirring overnight a white solid had formed. The reaction mixture was decanted away and the solid was washed with 50% brine in water (3×30 mL). The organic layer was separated, dried over sodium sulfate, filtered, and the filtrate was evaporated to afford the title intermediate 31 (413 mg, 112% crude) as a yellow-green oil; MS (+cAPCI) m/z 523 (m+Na+); 1H NMR (CDCl3), δ 7.70-8.00 (m, 2H), 7.20-7.40 (m, 3H), 5.40-5.50 (m, 3H), 4.55-4.95 (m, 5H), 1.20-2.60 (m, 20H).

Workup

  1. customTo a cold (−65 to −75° C.) solution
  2. additionwas added a solution
  3. customwas subsequently quenched with a 7:1 mixture of THF-water (8 mL)
  4. stirringto stir overnight (18 hours)
  5. stirringAfter stirring overnight a white solid
  6. customhad formed
  7. customThe reaction mixture was decanted away
  8. washthe solid was washed with 50% brine in water (3×30 mL)
  9. customThe organic layer was separated
  10. dry with materialdried over sodium sulfate
  11. filtrationfiltered
  12. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-65f6fcbb0bc844d88aa35d7491f7feda
Source dataset
uspto-grants-2011_11
Patent number
US08063240B2

Reaction notes

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