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

HRID 966981ノート

反応式

HRID 966981 の反応式
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

参加物

5

反応物 3

HCID 11776Triphenylphosphine2 回HCID 220568ethyl N-ethoxycarbonyliminocarbamate2 回HCID 21955304tert-Butyl 4-(2-hydroxyethyl)-4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5dc78274f4fb4b5ab123bcbfab1790fb
出典データセット
uspto-grants-2005_10
特許番号
US06953792B2

反応ノート

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