Triethylamine → (+/-)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonate

HRID 423629Notes

Reaction equation

HRID 423629 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]=[O:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:3].C[Mg]Br.[CH3:20][S:21](Cl)(=[O:23])=[O:22].[CH3:25]CN(CC)CC>>[CH3:20][S:21]([O:16][CH:15]([CH:12]1[CH2:13][CH2:14][N:9]([C:7]2[O:6][N:5]=[C:4]([CH:2]([CH3:1])[CH3:3])[N:8]=2)[CH2:10][CH2:11]1)[CH3:25])(=[O:23])=[O:22]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 866387441-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 86638745(+/-)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonateYield 83%

Procedure

(±)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonate (0.74 g, 49%) was prepared as a light brown oil from 1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde (1.07 g, 4.79 mmol) and methylmagnesium bromide (3M in Et2O, 3.51 mL, 10.54 mmol) then methanesulfonyl chloride (0.22 mL, 2.81 mmol) and Et3N (0.66 mL, 4.68 mmol) in a manner similar to Example 139, Steps 1-2. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.70-4.60 (m, 1H), 4.30-4.15 (m, 2H), 3.10-2.95 (m, 5H), 2.87 (septet, 1H, J=7.0 Hz), 1.95-1.70 (m, 3H), 1.55-1.35 (m, 5H), 1.26 (d, 6H, J=6.8 Hz).

Workup

  1. customThe crude product was used without further purification

Sources & evidence

ORD record
ord-cd2dfdcfee234d74898e370f71da0fc5
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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