2,4-Dichlorobenzaldehyde → 1-Cyclohexyl-3-[(2,4-dichloro-phenyl)-hydroxy-methyl]-pyrrolidin-2-one

HRID 2235274Notes

Reaction equation

[CH:1]1([N:7]2[CH2:11][CH2:10][CH2:9][C:8]2=[O:12])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Li+].CC([N-]C(C)C)C.[Cl:21][C:22]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=1[CH:24]=[O:25]>>[CH:1]1([N:7]2[CH2:11][CH2:10][CH:9]([CH:24]([C:23]3[CH:26]=[CH:27][C:28]([Cl:30])=[CH:29][C:22]=3[Cl:21])[OH:25])[C:8]2=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Reactant 3

HCID 134042,4-Dichlorobenzaldehyde

HCID 81278N-Cyclohexyl-2-pyrrolidone

HCID 2724682Lithium diisopropylamide

Product 1

HCID 116098311-Cyclohexyl-3-[(2,4-dichloro-phenyl)-hydroxy-methyl]-pyrrolidin-2-oneYield 53%

Procedure

Using the procedure to synthesize Example 1 and using reagents 1-cyclohexyl-pyrrolidin-2-one (500 mg, 3.0 mmol), LDA (2.0 M, 1.8 mL, 3.6 mmol) and 2,4-dichlorobenzaldehyde (630 mg, 3.6 mmol) affords 530 mg (53%) of the title compound as a white solid. Separate the diastereomers over silica gel (30% ethyl acetate in hexanes) Isomer 1 (Example 78): (25%) Mass spectrum (apci) m/z=342.0 (M+H). HPLC (5 to 95) Rt (Purity at 220 mn)=3.77 min (98%). Isomer 2 (Example 79): (28%) Mass spectrum (apci) m/z=342.0 (M+H). HPLC (5 to 95) Rt (Purity at 220 nm)=3.52 min (100%).

Workup

customto synthesize Example 1

Sources & evidence

ORD record: ord-e81d78d03a4f420b938731fe16bbea16
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07713979B2

Reaction notes

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