Triethylamine → (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 21768

反応式

HRID 21768 の反応式
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C>CS(C)=O>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

参加物

4

反応物 2

HCID 8471TriethylamineHCID 11096562Cbz-L-Prolinol

生成物 1

HCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester収率 70%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a stirred solution of N-Cbz-L-prolinol (5 g, 21.26 mmol, from steps 24b or 24c above)in 20 mL of anhydrous DMSO were added 8.89 mL (63.79 mmol) of triethylamine and 10.75 g (63.79 mmol) of SO3 -pyridine complex in 35 mL of DMSO. The reaction mixture was stirred at room temperature for 10 min, then poured into 200 mL of ice water. The mixture was extracted with ether, the extract was dried over Na2SO4 and concentrated to afford the title product, 3.058 g (70% yield).

後処理

  1. extractionThe mixture was extracted with ether
  2. dry with materialthe extract was dried over Na2SO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-dde2fa59cbf74121a07de79c5cab1323
出典データセット
uspto-grants-1995_06
特許番号
US05424444

関連ノート

読み込み中…