Iodide Ion → HCID 70200477、化合物

HRID 1276488

反応式

HRID 1276488 の反応式
[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]([CH2:21]OS(C3C=CC=CC=3)(=O)=O)[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[I-:32]>CC(C)=O>[C:1]1([S:7]([N:10]2[CH2:14][CH:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]([CH2:21][I:32])[CH2:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 30165Iodide IonHCID 867561541-(Benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine

生成物 1

HCID 70200477HCID 70200477、化合物収率 96.8%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of 234 mg (0.51 mmol) of 1-(benzenesulfonyl)-3-(SR)-benzenesulfonyloxymethyl-4-(SR)-phenylpyrrolidine (from Example 1, Step D) and 1.1 g (7.7 mmol) of sodiuim iodide in 8 mL of acetone was heated at reflux for 20 h. The reaction mixture was partitioned between 50 mL of ether and 30 mL of H2O and the layers were separated. The organic layer was washed with 30 mL of sat'd NaCl and dried over MgSO4. The aqueous layers were combined and extracted with 30 mL of ether. The extract was dried; the organic layers were combined. and concentrated in vacuo. Flash chromatography on 25 g of silica gel using 3:2 v/v hexanes/ether as the eluant afforded 211 mg (96%) of the title compound as an oil. 1H NMR (500 MHz, CDCl3): δ2.43 (t, J=9.8, 1H), 2.64-2.74 (m, 2H), 3.30 (dd, J=2.5, 7.8, 1H), 3.47 (q, J=6.7, 1H), 3.67-3.74 (3H), 7.05-7.95 (1OH). Mass Spectrum (NH3-CI): m/z 428 (M+1).

後処理

  1. temperatureat reflux for 20 h
  2. customThe reaction mixture was partitioned between 50 mL of ether and 30 mL of H2O
  3. customthe layers were separated
  4. washThe organic layer was washed with 30 mL of sat'd NaCl
  5. dry with materialdried over MgSO4
  6. extractionextracted with 30 mL of ether
  7. customThe extract was dried
  8. concentrationand concentrated in vacuo

出典と根拠

ORDレコード
ord-f466bd1aaae843c6860178b53a2e8d4d
出典データセット
uspto-grants-2000_12
特許番号
US06166037

関連ノート

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