Hydrochloric Acid → 4-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

HRID 1071502ノート

反応式

HRID 1071502 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([OH:13])[CH2:10][CH:9]1[CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][S:23]([CH3:22])(=[O:25])=[O:24])[CH2:10][CH:9]1[CH3:14])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 14117009tert-Butyl 4-hydroxy-2-methylpyrrolidine-1-carboxylate

生成物 1

HCID 197903964-Methanesulfonyloxy-2-methyl-pyrrolidine-1-carboxylic Acid T-butyl Ester

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
0 °C

実験手順

The 4-hydroxy-2-methyl-pyrrolidine-1-carboxylic acid t-butyl ester (110.89 mg, 0.55 mmol) was dissolved in anhydrous DCM and triethylamine (166.96 mg, 1.65 mmol, 0.23 mL) was added under argon. The reaction mixture was cooled to 0° C. and methanesulfonyl chloride (69.30 mg, 0.61 mmol, 0.05 mL) was added via syringe. The reaction was stirred at 0° C. for 30 min and then allowed to warm to room temp and stir for 12 h. The reaction was slowly poured into a 1N HCl solution and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water and brine then dried over MgSO4. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (3:1 hexane-ethyl acetate) Yield 135.21 mg.

後処理

  1. temperatureto warm to room temp
  2. stirringstir for 12 h
  3. extractionthe aqueous layer was extracted three times with ethyl acetate
  4. washThe combined organic layers were washed with water and brine
  5. dry with materialthen dried over MgSO4
  6. filtrationThe solution was filtered
  7. customthe solvent removed under reduced pressure
  8. customThe product was isolated by flash chromatography

出典と根拠

ORDレコード
ord-11707eb308254c3e8220457f94ec06db
出典データセット
uspto-grants-2005_06
特許番号
US06906067B2

反応ノート

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