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

HRID 2242944Notes

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-b28793f8d9384503ad3d484349e20b54
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674805B2

Reaction notes

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