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

HRID 966981노트

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HRID 966981 반응식
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

참가 물질

5

반응물 3

HCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 21955304tert-Butyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)piperidine-1-carboxylate

생성물 1

HCID 21955227Tert-butyl 2-oxa-8-azaspiro[4.5]decane-8-carboxylate수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5dc78274f4fb4b5ab123bcbfab1790fb
출처 데이터셋
uspto-grants-2005_10
특허 번호
US06953792B2

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