Trimethylsilyldiazomethane → 1-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylate

HRID 2191562ノート

反応式

HRID 2191562 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C:10]([NH2:16])([C:13]([OH:15])=[O:14])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[CH3:17][O:14][C:13]([C:10]1([NH2:16])[CH2:11][CH2:12][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:9]1)=[O:15]

参加物

5

反応物 2

HCID 167693TrimethylsilyldiazomethaneHCID 247303163-Amino-1-(tert-butoxycarbonyl)pyrrolidine-3-carboxylic acid

生成物 1

HCID 576862811-Tert-butyl 3-methyl 3-aminopyrrolidine-1,3-dicarboxylate収率 102.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

In a round-bottomed flask 3-aminopyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester (0.20 g, 0.87 mmol) was dissolved in dichloromethane (3.2 mL) and MeOH (1.6 mL). (Trimethylsilyl)diazomethane (2.0 M in hexanes, 0.75 mL, 1.5 mmol) was added dropwise and the reaction mixture was stirred at room temperature for 5 h. The reaction mixture was quenched with a small portion of acetic acid and concentrated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated aqueous Na2CO3. The aqueous layer was extracted with dichloromethane and the combined organics were dried over Na2SO4 and concentrated to afford 0.218 g of 3-amino-pyrrolidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester as a light yellow oil.

後処理

  1. customThe reaction mixture was quenched with a small portion of acetic acid
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with saturated aqueous Na2CO3
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined organics were dried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-22128106116043b78146309240c48f0e
出典データセット
uspto-grants-2012_12
特許番号
US08329699B2

反応ノート

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