Aluminium lithium hydride → Pyrrolidine, 3-(4,4-difluorocyclohexyl)-

HRID 2178507Notes

Reaction equation

HRID 2178507 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]1([F:20])[CH2:13][CH2:12][CH:11]([CH:14]2[CH2:18][NH:17][C:16](=O)[CH2:15]2)[CH2:10][CH2:9]1>C1COCC1>[F:20][C:8]1([F:7])[CH2:9][CH2:10][CH:11]([CH:14]2[CH2:15][CH2:16][NH:17][CH2:18]2)[CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 895005044-(4,4-Difluorocyclohexyl)pyrrolidin-2-one

Product 1

HCID 89500824Pyrrolidine, 3-(4,4-difluorocyclohexyl)-

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminium hydride (397.6 mg, 10.49 mmol, 2 eq) is added portionwise at 0° C. to a solution of 4-(4,4-difluorocyclohexyl)pyrrolidin-2-one a1-26 (assumed quantitative from previous step, 5.24 mmol, 1 eq) in dry THF (10 ml). The reaction mixture is allowed to warm to room temperature and stirred overnight, then quenched by water at 0° C. and filtered on celite. The solvent is evaporated under reduced pressure to afford 3-(4,4-difluorocyclohexyl)pyrrolidine a1-34.

Workup

  1. customquenched by water at 0° C.
  2. filtrationfiltered on celite
  3. customThe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-1dc32768f42c4b25921dce041eaafef1
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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