Cyclopropanemethanol → Benzyl rac-alpha-[[[1-[(cyclopropylmethoxy)carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

HRID 275605Notes

Reaction equation

HRID 275605 reaction equation
[CH2:1]([O:8][C:9]([CH:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][S:13]([C:16]([CH3:21])([CH3:20])[C:17](Cl)=[O:18])(=[O:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:29][CH2:30][CH:31]1[CH2:33][CH2:32]1>N1C=CC=CC=1>[CH:31]1([CH2:30][O:29][C:17]([C:16]([S:13]([CH2:12][CH:11]([CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])(=[O:14])=[O:15])([CH3:21])[CH3:20])=[O:18])[CH2:33][CH2:32]1

Participants

4

Reactant 2

HCID 75644CyclopropanemethanolHCID 20088482(RS)-2-[[2-[(Benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride

Product 1

HCID 54089114Benzyl rac-alpha-[[[1-[(cyclopropylmethoxy)carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

In an analogous manner to that described in Example 2, paragraph (c), by reacting (RS)-2-[[2-[(benzyloxy)carbonyl]-3-phenylpropyl]sulfonyl]-2-methylpropionyl chloride and hydroxymethylcyclopropane in pyridine there was obtained benzyl rac-α-[[[1-[(cyclopropylmethoxy)carbonyl]-1-methylethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil; MS: 459 (M+H)+.

Sources & evidence

ORD record
ord-4c899d8f38894dd0bfa9e102d1cf4ebb
Source dataset
uspto-grants-1995_02
Patent number
US05393875

Reaction notes

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