Potassium Carbonate → 3-(4'-Cyano-biphenyl-4-yloxymethyl)-1-(4-methoxy-benzoyl)-pyrrolidine-3-carboxylic acid ethyl ester

HRID 2060253Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:22]([O:24][C:25]([C:27]1([CH2:42]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:31][CH2:30][N:29]([C:32](=[O:41])[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)[CH2:28]1)=[O:26])[CH3:23]>CS(C)=O>[CH2:22]([O:24][C:25]([C:27]1([CH2:42][O:1][C:2]2[CH:3]=[CH:4][C:5]([C:8]3[CH:13]=[CH:12][C:11]([C:14]#[N:15])=[CH:10][CH:9]=3)=[CH:6][CH:7]=2)[CH2:31][CH2:30][N:29]([C:32](=[O:41])[C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)[CH2:28]1)=[O:26])[CH3:23]

Participants

Conditions

Temperature: 80 °C

Procedure

4′-hydroxy-4-biphenyl carbonitrile (107.0 g, 549 mmol) and potassium carbonate (94.9 g, 687 mmol) were added to a stirred solution of 1-(4-methoxy-benzoyl)-3-(toluene-4-sulfonyloxymethyl)-pyrrolidine-3-carboxylic acid ethyl ester (211.3 g, 457.8 mmol) (see Preparation 11) in dimethylsulphoxide (422 mL). The reaction mixture was heated at 80° C. for 18 hours then partitioned between ethyl acetate (2000 mL) and water (2000 mL). The organic layer was washed with water (2000 mL) then separated and concentrated under reduced pressure to afford the title compound as an orange oil (207.7 g, 93%). (>99.5% e.e.)

Workup

customthen partitioned between ethyl acetate (2000 mL) and water (2000 mL)
washThe organic layer was washed with water (2000 mL)
customthen separated
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-4b52a85abeee4f8f93c1ff4639321ad4
Source dataset: uspto-grants-2012_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08278343B2

Reaction notes

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