Thiophenol → tert-Butyl 4-[(phenylsulfanyl)methyl]piperidine-1-carboxylate

HRID 341514Notes

Reaction equation

HRID 341514 reaction equation
CS(O[CH2:6][CH:7]1[CH2:12][CH2:11][N:10]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][CH2:8]1)(=O)=O.[C:20]1([SH:26])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.FC(F)(F)CSCC1CCN(C(OC(C)(C)C)=O)CC1>>[C:20]1([S:26][CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[CH2:11][CH2:12]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 7969ThiophenolHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylate2×HCID 86710527HCID 86710527, compound

Product 1

HCID 66803236tert-Butyl 4-[(phenylsulfanyl)methyl]piperidine-1-carboxylateYield 144%

Procedure

tert-Butyl 4-[(phenylsulfanyl)methyl]piperidine-1-carboxylate was prepared from tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate (Intermediate 181, 0.320 g, 1.091 mmol) and thiophenol (0.117 mL, 1.145 mmol) according to the method described for Intermediate 183 to afford the title compound (0.483 g). 1H NMR (250 MHz, CDCl3) δ ppm 7.22 (5H, m), 4.10 (2H, m), 2.83 (2H d), 2.64 (2H, t), 1.84 (2H, d), 1.63 (1H, m), 1.44 (9H, s) and 1.17 (2H, m).

Sources & evidence

ORD record
ord-dd6d0858895443aaa180171fb67d5054
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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