Lithium Hydroxide → (2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

HRID 1666025ノート

反応式

HRID 1666025 の反応式
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([O:18]C)=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Li+].[OH-]>CO.O>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([OH:18])=[O:17])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 11219435(2S,4S)-1-tert-butyl 2-methyl 4-azidopyrrolidine-1,2-dicarboxylate

生成物 1

HCID 12094910(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid収率 100.2%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

Methyl(2S,4S)-1-Boc-4-azidopyrrolidine-2-carboxylate (10 g, 37 mmol) obtained in Step D of Preparation 1 was dissolved in MeOH (100 mL) and water (100 mL). LiOH (2.5 g, 111 mmol) was added thereto. The reaction solution was stirred for 3 hours at room temperature, concentrated in vacuo and acidify with 1N HCl. The solution was extracted with EtOAc. The extracted organic solution was washed with brine, dried over MgSO4 and concentrated in vacuo to give the title compound (9.5 g, 95%).

後処理

  1. concentrationconcentrated in vacuo
  2. extractionThe solution was extracted with EtOAc
  3. washThe extracted organic solution was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-9fc315ca0f734cbc9a2d6b35ab105623
出典データセット
uspto-grants-2011_10
特許番号
US08039622B2

反応ノート

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