Triethylamine → HCID 21224336, compound
Reaction equation
FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH2:16](N(CC)CC)[CH3:17].[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33]([CH2:39][OH:40])([C:36]([OH:38])=O)[CH2:32][CH2:31]1)=[O:29])([CH3:26])(C)C>C(OCC)C>[CH2:23]([O:27][C:28]([N:30]1[CH2:31][CH2:32][C:33]2([C:36](=[O:38])[O:40][CH2:39]2)[CH2:34][CH2:35]1)=[O:29])[CH2:26][CH2:16][CH3:17]Participants
Conditions
- Temperature
- 0 °C
Procedure
Trifluoromethanesulfonic anhydride (2.60 mL, 15.39 mmol), followed by triethylamine (4.30 mL, 30.78 mmol) was added to a slurry of N-(tert-butoxycarbonyl)-4-hydroxymethylpiperidine-4-carboxylic acid (3.80 g, 14.65 mmol) in anhydrous diethyl ether (27 mL) cooled to 0° C. The biphasic solution was stirred for 23 hours, warmed to room temperature, stirred an addition 1 hour, and the upper diethyl ether layer separated by decantation. The lower was extracted with additional portions of diethyl ether (2×100 mL), and the combined organic extracts washed with aqueous sodium bicarbonate solution (2×50 mL), dried over magnesium sulfate, and concentrated in vacuo to afford 7-(butoxycarbonyl)-2-oxa-7-azaspiro[3.5]nonan-1-one as a pale yellow oil (2.88 g, 82%). 1HNMR (CDCl3) δ 1.48 (s, 9H), 1.79-1.89 (m, 2H), 2.02-2.10 (m, 2H), 3.48-3.66 (m, 4H), 4.13 (s, 2H).
Workup
- temperaturewarmed to room temperature
- stirringstirred
- additionan addition 1 hour
- customthe upper diethyl ether layer separated by decantation
- extractionThe lower was extracted with additional portions of diethyl ether (2×100 mL)
- washthe combined organic extracts washed with aqueous sodium bicarbonate solution (2×50 mL)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-479a4fe7c8c844208ffbaa640897dccf
- Source dataset
- uspto-grants-1999_08
- Patent number
- US05932595
Reaction notes
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