tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate → N-(2-(pyrrolidin-3-ylmethoxy)phenyl)pyridine-2-sulfonamide trifluoroacetate

HRID 84165Notes

Reaction equation

HRID 84165 reaction equation
OCC1CCN(C(OC(C)(C)C)=O)C1.[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[NH:22]1[CH2:27][CH2:26][CH:25]([O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH:35][S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)(=[O:38])=[O:37])[CH2:24][CH2:23]1>>[F:15][C:16]([F:21])([F:20])[C:17]([OH:19])=[O:18].[NH:22]1[CH2:23][CH2:24][CH:26]([CH2:25][O:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[NH:35][S:36]([C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][N:40]=2)(=[O:37])=[O:38])[CH2:27]1

Participants

3

Reactant 2

HCID 5237175tert-Butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylateHCID 67607774N-(2-(piperidin-4-yloxy)phenyl)pyridine-2-sulfonamide trifluoroacetate

Product 1

HCID 67609894N-(2-(pyrrolidin-3-ylmethoxy)phenyl)pyridine-2-sulfonamide trifluoroacetateYield 39%

Procedure

Intermediate 6b (solid) is prepared using tert-butyl 3-(hydroxymethyl)pyrrolidine-1-carboxylate instead of tert-butyl 4-hydroxypiperidine-1-carboxylate using the procedure described for 6a (yield: 39% over the 4 steps).

Sources & evidence

ORD record
ord-85a26538ca064fc29b14f3603b7befd8
Source dataset
uspto-grants-2014_09
Patent number
US08846930B2

Reaction notes

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