2-Chlorophenol → HCID 67315305, compound

HRID 1010707Notes

Reaction equation

HRID 1010707 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[CH2:21][O:22]S(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:10][C@@H:9]1[CH2:21][O:22][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[Cl:27])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 72452-ChlorophenolHCID 10796Cesium carbonateHCID 86635143HCID 86635143, compound

Product 1

HCID 67315305HCID 67315305, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

12.5 Reaction of 1.5 g of 1-tert-butyloxycarbonyl-(2R,4S)-2-(methylsulfonyloxymethyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine with 560 μl of 2-chlorophenol and 1.19 g of caesium carbonate in 15 ml of DMF under standard conditions gives 751 mg of (2R,4S)-1-tert-butyloxycarbonyl-2-(2-chlorophenoxymethyl)-4-(tert-butyldimethylsilyloxy)pyrrolidine. 223 mg of the silyl-eliminated product (2R,4S)-1-tert-butyloxycarbonyl-2-(2-chlorophenoxymethyl)-4-hydroxypyrrolidine are formed as by-product.

Sources & evidence

ORD record
ord-65696af53fb44f93a48e0edc1a03c8c8
Source dataset
uspto-grants-2011_07
Patent number
US07977343B2

Reaction notes

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