1,2-Dichloroethane → (2S,4S)-1-Boc-4-azido-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine

HRID 1666026ノート

反応式

HRID 1666026 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]([OH:18])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(C(C)C)C(C)C.[CH3:28][N:29]1[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+:14]=[N-:15])[CH2:10][C@H:9]1[C:16]([N:32]1[CH2:33][CH2:34][N:29]([CH3:28])[CH2:30][CH2:31]1)=[O:18])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 12094910(2S,4S)-4-azido-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

生成物 1

HCID 86641588(2S,4S)-1-Boc-4-azido-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine収率 98.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(2S,4S)-1-Boc-4-azidopyrrolidine-2-carboxylic acid (9.5 g, 35 mmol) obtained in Step A was dissolved in DMF (30 mL). After DIPEA (1.15 mL, 6.70 mmol) was added thereto, 1-methylpiperazine (5.81 mL, 52.5 mmol), HOBT (7 g, 52.5 mmol) and EDC (10.2 g, 52.5 mmol) were added thereto, in turn. The reaction solution was stirred for 12 hours at room temperature and concentrated in vacuo. The residue was diluted with EtOAc and washed with saturated NaHCO3 aqueous solution, water and 1N HCl. The extracted organic solution was dried over MgSO4 and concentrated in vacuo. The residue was purified by column chromatography (eluent: MC/MeOH=10/1) to give the title compound (11.67 g, 93%).

後処理

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with EtOAc
  3. washwashed with saturated NaHCO3 aqueous solution, water and 1N HCl
  4. dry with materialThe extracted organic solution was dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (eluent: MC/MeOH=10/1)

出典と根拠

ORDレコード
ord-9c748af8acad442e92934418dd237efe
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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