Water → phenyl(pyrrolidin-2-yl)methanol

HRID 1413114Notes

Reaction equation

[C:1]([CH:9]1[NH:13][C:12](=O)[CH2:11][CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:2]1([CH:1]([CH:9]2[CH2:10][CH2:11][CH2:12][NH:13]2)[OH:8])[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

65.6 g of 5-benzoyl-2-pyrrolidone prepared as indicated in above part (a) are added in small fractions, under a nitrogen atmosphere, to a suspension of 26.4 g of lithium aluminium hydride in 4 liters of anhydrous tetrahydrofuran. The mixture is then refluxed with stirring for 2 hours. It is then cooled to 0° C. and then are slowly added 30.5 ml of water, then 11 ml of a 10 N solution of sodium hydroxide and finally 110 ml of water. After having stirred for 2 hours at the ambient temperature, the precipitate formed is separated by filtration. The filtrate obtained is dried over magnesium sulfate and the solvent is distilled under reduced pressure. 53 g of α-phenyl-2-pyrrolidine methanol are obtained. These 53 g are recrystallized from 580 ml of isopropyl ether. 36 g of α-phenyl-2-pyrrolidine methanol (erythro) melting at 110° C. are thus obtained.

Workup

temperatureThe mixture is then refluxed
stirringAfter having stirred for 2 hours at the ambient temperature
customthe precipitate formed
customis separated by filtration
customThe filtrate obtained
dry with materialis dried over magnesium sulfate
distillationthe solvent is distilled under reduced pressure

Sources & evidence

ORD record: ord-1cd372f57d2144c7a99f3865a3f5bcee
Source dataset: uspto-grants-1981_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04248884

Reaction notes

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