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

HRID 852684노트

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HRID 852684 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 24, 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-01a3a0d0f48845b78e6ea94a3409b585
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07253205B2

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