Aluminium lithium hydride → HCID 58171625, compound

HRID 1752290Notes

Reaction equation

HRID 1752290 reaction equation
[OH:1][C:2]([CH3:17])([CH3:16])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][NH:7][C:6](=O)[CH2:5]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:17][C:2]([OH:1])([CH3:16])[CH2:3][C:4]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:5][CH2:6][NH:7][CH2:8]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 581716052-Pyrrolidinone, 4-(2-hydroxy-2-methylpropyl)-4-phenyl-

Product 1

HCID 58171625HCID 58171625, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-hydroxy-2-methylpropyl)-4-phenylpyrrolidin-2-one (crude, 2.17 g, 9.3 mmol) in anhydrous THF (40 mL) was added LiAlH4 (1.42 g, 37.3 mmol) at −10° C. in a dry-ice/acetone bath. The reaction mixture was refluxed overnight. LC-MS showed that about 90% of desired product was produced. The reaction mixture was diluted with anhydrous THF (200 mL) and filtered through Celite. The filter cake was washed several times with anhydrous THF. The filtrate was concentrated to dryness to give crude 2-methyl-1-(3-phenylpyrrolidin-3-yl)propan-2-ol (1.34 g, 67%), which was used directly for next step without purification. 1H NMR (CDCl3 400 MHz): δ 7.28-7.22 (m, 4H), 7.16-7.12 (m, 1H), 3.82 (s, br, 1H), 3.24-3.16 (m, 2H), 3.11 (m, 1H), 2.95 (m, 1H), 2.26-2.13 (m, 2H), 1.98 (s, 2H), 1.09 (s, 3H), 1.05 (s, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight

Sources & evidence

ORD record
ord-ca93a6d6a5614501b0d98f4e0df222c5
Source dataset
uspto-grants-2015_10
Patent number
US09163012B2

Reaction notes

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