Triphenylphosphine → Tert-butyl 2-oxa-8-azaspiro[4.5]decane-8-carboxylate

HRID 966981Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.O[CH2:14][CH2:15][C:16]1([CH2:29][OH:30])[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH2:29]1[C:16]2([CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:20][CH2:21]2)[CH2:15][CH2:14][O:30]1

Participants

Conditions

Temperature: 0 °C

Procedure

Diethyl azodicarboxylate (183 μl, 1.16 mmol) in tetrahydrofuran (0.5 mL) was added dropwise to a stirred, cooled (0° C.) solution of 1,1-dimethylethyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)-1-piperidinecarboxylate (Description 42, 250 mg, 0.96 mmol) and triphenylphosphine (303 mg, 1.16 mmol) in tetrahydrofuran (10 mL) and the mixture was stirred at 0° C. for 90 minutes then at room temperature overnight. The mixture was cooled to 0° C. and further triphenylphosphine (126 mg, 0.48 mmol) and diethyl azodicarboxylate (76 μl, 0.48 mmol) were added. The mixture was stirred at room temperature for 2.5 hours, then the solvent was evaporated under reduced pressure and the residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (80:20), to give the title compound as a colorless oil (150 mg, 65%). m/z (ES+) 186 (M+1-C4H8).

Workup

customat room temperature
customovernight
temperatureThe mixture was cooled to 0° C.
stirringThe mixture was stirred at room temperature for 2.5 hours
customthe solvent was evaporated under reduced pressure
customthe residue was purified by flash column chromatography on silica gel
washeluting with isohexane/EtOAc (80:20)

Sources & evidence

ORD record: ord-5dc78274f4fb4b5ab123bcbfab1790fb
Source dataset: uspto-grants-2005_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06953792B2

Reaction notes

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