m-Chloroperbenzoic acid → Benzyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

HRID 1694867ノート

反応式

HRID 1694867 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13](=[CH2:16])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)[O-:18].[Na+].ClC1C=CC=C(C(OO)=O)C=1>ClCCl.S([O-])([O-])=O.[Na+].[Na+]>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]2([O:18][CH2:16]2)[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 184122471-Cbz-3-methylenepyrrolidine

生成物 1

HCID 71649494Benzyl 1-oxa-5-azaspiro[2.4]heptane-5-carboxylate

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 24437Sodium Sulfite溶媒

実験手順

A solution 3-methylen-pyrrolidine-1-carboxylic acid benzyl ester (WO9624593) in 5 ml of dichloromethane was treated with 2.16 g sodium bicarbonate (MW: 84.01 26.28 mmol) and 2.47 g of 80% m-chlor-perbenzoic acid (MW: 172.57, 11.48 mmol). The reaction mixture was stirred at room temperature for three hours. The reaction mixture was diluted with 20 ml of a saturated aqueous sodium sulfite solution and 45 ml of dichloromethane. The organic layer was successively washed with 30 ml of an aqueous saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate. The residue was purified by chromatography on silica (1/1 ethyl acetate/n-hexane) to afford a off white solid. Yield: 440 mg, 57%. MS: 234.1 (M+H)+, Method ESI+.

後処理

  1. washThe organic layer was successively washed with 30 ml of an aqueous saturated sodium bicarbonate solution and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. customThe residue was purified by chromatography on silica (1/1 ethyl acetate/n-hexane)
  4. customto afford a off white solid

出典と根拠

ORDレコード
ord-ba69888c4b4d4f279910ff83a2fdbc32
出典データセット
uspto-grants-2012_04
特許番号
US08158797B2

反応ノート

読み込み中…