1-Boc-piperidine-3-carboxaldehyde → Tert-butyl 3-(2-methoxyethenyl)-1-piperidinecarboxylate

HRID 1767333노트

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HRID 1767333 반응식
[Cl-].[CH3:2][O:3][CH2:4][PH3+].CC(C)([O-])C.[K+].[CH:12]([CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15]1)=O>C1COCC1>[CH3:2][O:3][CH:4]=[CH:12][CH:14]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:24])([CH3:26])[CH3:25])=[O:21])[CH2:15]1

참가 물질

5

반응물 3

HCID 99644481-Boc-piperidine-3-carboxaldehydeHCID 22258747(Methoxymethyl)phosphonium chlorideHCID 23665647Potassium tert-butoxide

생성물 1

HCID 69249758Tert-butyl 3-(2-methoxyethenyl)-1-piperidinecarboxylate수율 48.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

To a suspension of methoxymethylphosphonium chloride (5.14 g, 15 mmol) in THF (18 mL) was added potassium tert-butoxide (1.98 g, 15 mmol) at 0° C., and the mixture was stirred at 0° C. for 0.5 hr. A solution of tert-butyl 3-formyl-1-piperidinecarboxylate (2.13 g, 10 mmol) in THF (8 mL) was added dropwise at −20° C., and the resulting mixture was stirred at 0° C. to room temperature overnight. The mixture was partitioned between toluene and water. The separated organic phase was washed with brine, dried over Na2SO4, filtered, and evaporated. Purification by column chromatography on silica gel (hexane/ethyl acetate=5/1) gave tert-butyl 3-(2-methoxyethenyl)-1-piperidinecarboxylate as a colorless oil (1.16 g, yield; 48%).

후처리

  1. stirringthe resulting mixture was stirred at 0° C. to room temperature overnight
  2. customThe mixture was partitioned between toluene and water
  3. washThe separated organic phase was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customPurification by column chromatography on silica gel (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-95843ff01f00456db942e2dbda159f82
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07232909B2

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