Tert-butyl 4-hydroxypiperidine-1-carboxylate → HCID 68277919, compound
Reaction equation
CS([O:5][CH2:6][CH2:7][CH2:8][C:9]1[N:10]=[C:11]([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=2)[O:12][C:13]=1[CH3:14])(=O)=O.O[CH:26]1[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]1.CC(C)([O-])C.[K+]>CN(C)C=O>[C:35]([O:34][C:32]([N:29]1[CH2:30][CH2:31][CH:26]([O:5][CH2:6][CH2:7][CH2:8][C:9]2[N:10]=[C:11]([C:15]3[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=3)[O:12][C:13]=2[CH3:14])[CH2:27][CH2:28]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]Participants
Conditions
- Temperature
- 35 °C
Procedure
To a solution of methyl 4-[4-[3-(methanesulfonyloxy)propyl]-5-methyl-1,3-oxazol-2-yl]benzoate (630 mg, 1.78 mmol, 1.00 equiv) and tert-butyl 4-hydroxypiperidine-1-carboxylate (1 g, 4.97 mmol, 2.79 equiv) in N,N-dimethylformamide (20 mL) maintained under nitrogen at 35° C. was added potassium tert-butoxide (350 mg, 3.12 mmol, 1.75 equiv) in 20 min. The resulting solution was stirred at 35° C. for another 35 min then the reaction was quenched with 50 mL of water. The pH value of the solution was adjusted to 2-3 with 2N hydrochloric acid. The resulting solution was extracted with 50 mL of ethyl acetate. The organic layer was washed with 2×50 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 1.0 g of crude 4-(4-(3-(1-(tert-butoxycarbonyl)piperidin-4-yloxy)propyl)-5-methyloxazol-2-yl)benzoic acid as a white solid. LC-MS: (ES, m/z): 445[M+H]+, 389, 115.
Workup
- customthe reaction was quenched with 50 mL of water
- extractionThe resulting solution was extracted with 50 mL of ethyl acetate
- washThe organic layer was washed with 2×50 mL of brine
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-f167d19ff87745869872d1ce9ff26217
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296732B2
Reaction notes
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