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

HRID 423610Notes

Reaction equation

HRID 423610 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]([OH:17])[CH3:16])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:3].[CH3:18][S:19](Cl)(=[O:21])=[O:20].CCN(CC)CC>>[CH3:18][S:19]([O:17][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)[CH3:16])(=[O:21])=[O:20]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66672695(+/-)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethanol

Product 1

HCID 86638745(+/-)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonateYield 102.5%

Conditions

Temperature
0 °C

Procedure

A solution of (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethanol (0.39 g) in CH2CH2 (35 mL) at 0° C. was treated with methanesulfonyl chloride (0.26 mL, 3.26 mmol) and Et3N (0.69 mL, 4.89 mmol) and stirred at 0° C. for 1 h then room temperature for 15 h. The mixture was diluted with CH2CH2 (80 mL), washed with 1M NaH2PO4 (50 mL×2) and brine (35 mL), and dried over Na2SO4 and concentrated to afford crude (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonate (0.53 g, 100%) as a light brown oil. The crude product was used without further purification. 1H NMR (400 MHz, CDCl3): δ 4.75-4.65 (m, 1H), 4.30-4.15 (m, 2H), 3.10-2.95 (m, 5H), 2.89 (septet, 1H, J=7.0 Hz), 1.95-1.70 (m, 3H), 1.55-1.35 (m, 5H), 1.28 (d, 6H, J=6.9 Hz).

Workup

  1. waitroom temperature for 15 h
  2. additionThe mixture was diluted with CH2CH2 (80 mL)
  3. washwashed with 1M NaH2PO4 (50 mL×2) and brine (35 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dcc4b35364d34b28aa66e06b35cdf17a
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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