Aluminium lithium hydride → 1-Benzyl-5,5-dimethylpyrrolidin-3-amine

HRID 1366616Notes

Reaction equation

CO/[N:3]=[C:4]1/[C:5](=O)[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:7]([CH3:10])([CH3:9])[CH2:8]/1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:9][C:7]1([CH3:10])[N:6]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:5][CH:4]([NH2:3])[CH2:8]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a 0° C. solution of (3E)-5,5-dimethyl-1-(phenylmethyl)-2,3-pyrrolidinedione 3-(O-methyloxime) (4.2872 g, 17.41 mmol) in THF (90 mL) was added LiAlH4 (2.64 g, 69.57 mmol) portionwise. The mixture was heated at 70° C. and stirred for 6.5 h. The mixture was then cooled to room temperature and quenched by addition of Na2SO4.10H2O (3 g), followed by 1 N aq. NaOH (100 mL). The mixture was extracted with Et2O (2×150 mL), and the combined organic phase was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo. The residue was diluted with DCM (200 mL), and the mixture was dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to give crude racemic 5,5-dimethyl-1-(phenylmethyl)-3-pyrrolidinamine (3.2293 g, 86%) as a light yellow oil. LCMS: (M+H)+: 205.2.

Workup

temperatureThe mixture was then cooled to room temperature
customquenched by addition of Na2SO4.10H2O (3 g)
extractionThe mixture was extracted with Et2O (2×150 mL)
dry with materialthe combined organic phase was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
additionThe residue was diluted with DCM (200 mL)
dry with materialthe mixture was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5a4b5d8a0ef44601930b7e6584e2d577
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893056B2

Reaction notes

Loading…