Ethyl [(phenoxycarbonyl)oxy]acetate → 2-(Ethyloxy)-2-oxoethyl 3-[(1-naphthalenyloxy)methyl]-1-pyrrolidinecarboxylate

HRID 912745Notes

Reaction equation

[C:1]1([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][NH:15][CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.C1([O:24][C:25]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=O)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]1([O:11][CH2:12][CH:13]2[CH2:17][CH2:16][N:15]([C:25]([O:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:24])[CH2:14]2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of 0.20 g (0.88 mmol) of 3-[(1-naphthalenyloxy)methyl]pyrrolidine, prepared in Step 12.2., and 0.35 g (1.5 mmol) of ethyl [(phenyloxycarbonyl)oxy]acetate, prepared in accordance with Example 1.1, in 6 ml of toluene is heated at 60° C. overnight. It is evaporated to dryness and the residue is taken up in a mixture of water, dichloromethane and saturated aqueous sodium hydrogen carbonate solution. The organic phase is decanted, dried over sodium sulfate and evaporated to dryness. The residue is purified by chromatography on a silica gel column, eluting with dichloromethane and then with a 99/1 mixture of dichloromethane and methanol. This gives 0.24 g of product in oil form, which is used as it is in the following step.

Workup

customIt is evaporated to dryness
additionthe residue is taken up in a mixture of water, dichloromethane and saturated aqueous sodium hydrogen carbonate solution
customThe organic phase is decanted
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe residue is purified by chromatography on a silica gel column
washeluting with dichloromethane
additionwith a 99/1 mixture of dichloromethane and methanol

Sources & evidence

ORD record: ord-d818b239992b43d19c2d13945a7f12ca
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026258B2

Reaction notes

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