Diisobutylaluminumhydride → (S,E)-tert-butyl 2-(4-(hydroxymethyl)styryl)pyrrolidine-1-carboxylate

HRID 923445Notes

Reaction equation

C[O:2][C:3]([C:5]1[CH:24]=[CH:23][C:8](/[CH:9]=[CH:10]/[C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[CH:7][CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C>ClCCl>[OH:2][CH2:3][C:5]1[CH:6]=[CH:7][C:8](/[CH:9]=[CH:10]/[C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])=[CH:23][CH:24]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of the product of Example 149B (1.0 g, 3.02 mmol) dissolved in dichloromethane (20 mL) and cooled to −78° C. was added diisobutylaluminum hydride (1.0M in dichloromethane, 10.56 mL, 10.56 mmol) dropwise and the resultant solution stirred at −78° C. for 10 minutes, the cooling bath was then removed and after the reaction reached room temperature it was maintained at this temperature for an additional 1 hour. The solution had acetone (1 mL) added then EtOAc added to it and the mixture extracted with aqueous sodium potassium tartrate solution. The organic extract was then dried, filtered, and concentrated to afford 0.9 g (98%) of the title compound.

Workup

customthe cooling bath was then removed
customreached room temperature
temperaturewas maintained at this temperature for an additional 1 hour
additionadded
additionEtOAc added to it
extractionthe mixture extracted with aqueous sodium potassium tartrate solution
extractionThe organic extract
customwas then dried
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-08b5ac2ffbc24541bead2b0e8f430926
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278922B2

Reaction notes

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