Ethanolamine → 1-(2-Hydroxyethyl)-3,3-diphenylpyrrolidin-2-one

HRID 1667133

Reaction equation

[C:1]1([C:7]2([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][CH2:10][O:9][C:8]2=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:19][CH2:20][CH2:21][OH:22]>[Cl-].[Zn+2].[Cl-]>[OH:22][CH2:21][CH2:20][N:19]1[CH2:10][CH2:11][C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:8]1=[O:9]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 3,3-diphenyldihydrofuran-2(3H)-one (0.5 g, 2.098 mmol), 2-aminoethanol (1282 mg, 20.98 mmol) and zinc chloride (0.23 g, 1.679 mmol) was heated neat at 100° C. for 16 hours. The reaction mixture was cooled and partitioned in H2O/ethyl acetate. The organic layer was separated, dried over MgSO4, and concentrated to yield the title compound. 1H NMR (400 MHz, CDCl3) δ ppm 7.32 (m, 8H), 7.23 (m, 2H), 3.81 (q, J=5.42 Hz, 2H), 3.52 (t, J=5.42 Hz, 2H), 3.45 (t, J=6.44 Hz, 2H), 2.85 (t, J=5.52 Hz, 1H), 2.79 (t, J=6.44 Hz, 2H); MS (ESI+) m/z 282 (M+H)+.

Workup

temperatureThe reaction mixture was cooled
custompartitioned in H2O/ethyl acetate
customThe organic layer was separated
dry with materialdried over MgSO4
concentrationconcentrated

Sources & evidence

ORD record: ord-ac44c9d704d04ff297f65de067ef0708
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044069B2

Linked notes

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