Formaldehyde → 1-Benzyl-5-(hydroxymethyl)pyrrolidin-2-one

HRID 2050937Notes

Reaction equation

HRID 2050937 reaction equation
[OH:1][CH2:2][C@H:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[CH2:5][CH2:4]1.CO[C@](C1C=CC=CC=1)(C(F)(F)F)C(O)=O.C=O>>[OH:1][CH2:2][CH:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6](=[O:15])[CH2:5][CH2:4]1

Participants

4

Reactant 3

HCID 712FormaldehydeHCID 6992788alpha-Methoxy-alpha-trifluoromethylphenylacetic acid, (-)-HCID 10442943(S)-1-Benzyl-5-hydroxymethyl-2-pyrrolidinone

Product 1

HCID 5630611-Benzyl-5-(hydroxymethyl)pyrrolidin-2-one

Procedure

The optical purity of the (S)-5-(hydroxymethyl)-1-(phenylmethyl)-2-pyrrolidinone was established by formation of the ester derived from (S)-(-)-α-methoxy-α-(trifluoromethyl)phenylacetic acid ((-)-MTPA) following the procedure of Mosher, et al. (J. Org. Chem. 1969, 34, 2543). A single diastereomeric ester, as judged by 1H NMR and TLC, was obtained, and could readily be differentiated from the diastereomeric mixture (by the doubling of the CH2N and CH2O signals in the 1H NMR) produced when racemic 5-(hydroxymethyl)-1-(phenylmethyl)-2-pyrrolidinone was used to form the (-)-MTPA ester.

Workup

  1. customwas obtained

Sources & evidence

ORD record
ord-f1ba3e151907454596a89e401942ec93
Source dataset
uspto-grants-1991_05
Patent number
US05015653

Reaction notes

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