4-Ethylbenzene-1-sulfonyl chloride → (2RS,5SR)-[1-(4-Ethyl-benzenesulfonyl)-5-(4-fluoro-phenyl)-pyrrolidin-2-yl]-methanol

HRID 1357121

Reaction equation

HRID 1357121 reaction equation
FC1C=CC(C2NC(C(OC)=O)CC2)=CC=1.C(C1C=CC(S(Cl)(=O)=O)=CC=1)C.[F:29][C:30]1[CH:35]=[CH:34][C:33]([CH:36]2[N:40]([S:41]([C:44]3[CH:49]=[CH:48][C:47]([CH2:50][CH3:51])=[CH:46][CH:45]=3)(=[O:43])=[O:42])[CH:39]([C:52](OC)=[O:53])[CH2:38][CH2:37]2)=[CH:32][CH:31]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:50]([C:47]1[CH:46]=[CH:45][C:44]([S:41]([N:40]2[CH:36]([C:33]3[CH:32]=[CH:31][C:30]([F:29])=[CH:35][CH:34]=3)[CH2:37][CH2:38][CH:39]2[CH2:52][OH:53])(=[O:43])=[O:42])=[CH:49][CH:48]=1)[CH3:51]

Participants

5

Reactant 4

HCID 5709594-Ethylbenzene-1-sulfonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 67257147methyl (2RS,5SR)-5-(4-fluoro-phenyl)-pyrrolidine-2-carboxylateHCID 86584369methyl (2RS,5SR)-5-(4-fluoro-phenyl)-1-(4-ethyl-benzenesulfonyl)-pyrrolidine-2-carboxylate

Product 1

HCID 69596851(2RS,5SR)-[1-(4-Ethyl-benzenesulfonyl)-5-(4-fluoro-phenyl)-pyrrolidin-2-yl]-methanol

Procedure

The title compound, pale yellow oil, MS: m/e=363 (M+) was prepared in accordance with the general methods of example 1d and 84a from methyl (2RS,5SR)-5-(4-fluoro-phenyl)-pyrrolidine-2-carboxylate and 4-ethyl-benzenesulfonyl chloride and subsequent reduction of methyl (2RS,5SR)-5-(4-fluoro-phenyl)-1-(4-ethyl-benzenesulfonyl)-pyrrolidine-2-carboxylate with lithium aluminum hydride according to the general method of example 2.

Sources & evidence

ORD record
ord-a5fdca9f330045f7bba2afe8e81584c8
Source dataset
uspto-grants-2003_07
Patent number
US06589978B2

Linked notes

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