2-(4-Chlorophenyl)ethyl 4-methylbenzenesulfonate → (S)-N-(1-(2-(4-chlorophenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide

HRID 992279Notes

Reaction equation

HRID 992279 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]23[CH2:18][CH:13]4[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]4)[CH2:10]2)[CH2:16]3)=[O:8])[CH2:2]1.C1(C)C=CC(S(O[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=2)(=O)=O)=CC=1>>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][CH2:29][N:1]2[CH2:5][CH2:4][C@H:3]([NH:6][C:7]([C:9]34[CH2:18][CH:13]5[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]5)[CH2:10]3)[CH2:16]4)=[O:8])[CH2:2]2)=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 2447732-(4-Chlorophenyl)ethyl 4-methylbenzenesulfonateHCID 49760538(S)-N-(pyrrolidin-3-yl)-1-adamantanecarboxamide

Product 1

HCID 9930106(S)-N-(1-(2-(4-chlorophenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamideYield 22%

Procedure

(S)-N-(Pyrrolidin-3-yl)-1-adamantanecarboxamide (0.38 g) and 2-(4-chlorophenyl)ethyl p-toluenesulfonate (0.57 g) were reacted under the same conditions as in Example 1 to give (S)-N-(1-(2-(4-chlorophenyl)ethyl)pyrrolidin-3-yl)-1-adamantanecarboxamide (0.13 g), melting point 94-95° C.

Sources & evidence

ORD record
ord-0da4b39d10c04a7eb1bb7c8b09744445
Source dataset
uspto-grants-2002_10
Patent number
US06468998B1

Reaction notes

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