Methyl iodide → Tert-butyl 3-methoxy-4-methylenepyrrolidine-1-carboxylate

HRID 2040914노트

반응식

HRID 2040914 반응식
[OH:1][CH:2]1[C:6](=[CH2:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[H-].[Na+].[CH3:17]I>C1COCC1>[CH3:17][O:1][CH:2]1[C:6](=[CH2:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 11446960Tert-butyl 3-hydroxy-4-methylidenepyrrolidine-1-carboxylate

생성물 1

HCID 57493865Tert-butyl 3-methoxy-4-methylenepyrrolidine-1-carboxylate수율 60%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of tert-butyl 3-hydroxy-4-methylenepyrrolidine-1-carboxylate (0.257 g, 1.29 mmol; prepared as described by Alcaraz, Lilian; Cridland, Andrew; Kinchin, Elizabeth Organic Letters, 2001, vol. 3, #25 p. 4051-4054) in 8 mL of THF, stirred at r.t. under a nitrogen atmosphere was added NaH. After 0.5 h stirring at r.t., methyl iodide (0.057 g, 1.42 mmol) was added and the resulting mixture stirred at r.t. for 2 h. After overnight resting, the reaction was quenched with water, extracted with EtOAc which was washed with brine, dried over Na2SO4 and evaporated to dryness affording a crude, purified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 9:1 to 7:3) giving 165 mg of the title compound. Yield: 60%.

후처리

  1. stirringthe resulting mixture stirred at r.t. for 2 h
  2. waitAfter overnight resting
  3. customthe reaction was quenched with water
  4. extractionextracted with EtOAc which
  5. washwas washed with brine
  6. dry with materialdried over Na2SO4
  7. customevaporated to dryness
  8. customaffording a crude
  9. custompurified by means of automated flash chromatography (SP01®TM-Biotage; gradient Petroleum Ether-EtOAc from 9:1 to 7:3)

출처 및 근거

ORD 기록
ord-9462a9710bf442889f93444c3126d25b
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580962B2

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