Trimethylsilyl isocyanate → (R)-tert-butyl 3-ureidopyrrolidine-1-carboxylate

HRID 57541ノート

反応式

HRID 57541 の反応式
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.[Si]([N:18]=[C:19]=[O:20])(C)(C)C.CCN(C(C)C)C(C)C>ClCCl>[NH:1]([C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1)[C:19]([NH2:18])=[O:20]

参加物

5

反応物 3

HCID 70696Trimethylsilyl isocyanateHCID 81531DiisopropylethylamineHCID 854070(R)-(+)-1-Boc-3-aminopyrrolidine

生成物 1

HCID 71113416(R)-tert-butyl 3-ureidopyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (R)-tert-butyl 3-aminopyrrolidine-1-carboxylate (180 mg, 1 mmol) in dichloromethane was added TMS-NCO (1 g, 8.7 mmol) and DIPEA (1.2 g, 10 mmol). The mixture was stirred at room temperature overnight, then was concentrated in vacuo. The residue was treated with EtOAc/H2O, the organic layer was combined, washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give the crude title compound.

後処理

  1. concentrationwas concentrated in vacuo
  2. additionThe residue was treated with EtOAc/H2O
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-03b908eb6c974305becfdd62d3cb84c4
出典データセット
uspto-grants-2016_09
特許番号
US09434726B2

反応ノート

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