Phenol → tert-Butyl (R)-3-phenoxypyrrolidine-1-carboxylate

HRID 1176542Notes

Reaction equation

HRID 1176542 reaction equation
C1(C)C=CC(S([O:10][C@H:11]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12]2)(=O)=O)=CC=1.[C:24]1(O)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[O:10]([C@@H:11]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:12]1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 996PhenolHCID 57957824(S)-3-(Toluene-4-sulfonyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 86610018tert-Butyl (R)-3-phenoxypyrrolidine-1-carboxylate

Procedure

Analogously to Method G, 1.01 g of tert-butyl (S)-3-(toluene-4-sulphonyloxy)pyrrolidine-1-carboxylate and 0.418 g of phenol are reacted. The title compound is obtained as a colourless oil. Rf=0.47 (2:1 EtOAc-heptane); Rt=4.88.

Sources & evidence

ORD record
ord-899e7d21194b4ee38a7bff879b32f483
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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