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

HRID 2040914ノート

反応式

HRID 2040914 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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%.

後処理

  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)

出典と根拠

ORDレコード
ord-9462a9710bf442889f93444c3126d25b
出典データセット
uspto-grants-2013_11
特許番号
US08580962B2

反応ノート

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