1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde → (+/-)-1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethanol
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].[CH3:17][Mg]Br>C1COCC1>[CH3:3][CH:2]([C:4]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([CH:15]([OH:16])[CH3:17])[CH2:11][CH2:10]2)[O:6][N:5]=1)[CH3:1]Participants
4
Procedure
A solution of 1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinecarbaldehyde (1.1 g, 4.93 mmol) in THF (25 mL) at −10° C. was treated dropwise with methylmagnesium bromide (3M in Et2O, 3.94 mL, 11.8 mmol). The mixture was stirred at −10° C. to −5° C. over a 2 h period. The reaction was carefully quenched by the addition of saturated aqueous NH4Cl and the aqueous was extracted with ether (6 mL×2). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. The crude material was purified by chromatography on a silica gel column eluted with 0 to 70% EtOAc/hexanes to give 0.39 g (33%) of (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethanol as a light yellow oil.
Workup
- customThe reaction was carefully quenched by the addition of saturated aqueous NH4Cl
- extractionthe aqueous was extracted with ether (6 mL×2)
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe crude material was purified by chromatography on a silica gel column
- washeluted with 0 to 70% EtOAc/hexanes
Sources & evidence
- ORD record
- ord-005f9e3423184321b6fc1ef5621ae429
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08101634B2
Reaction notes
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