Water → Benzyl 3-allyl-4-oxocyclopentylcarbamate

HRID 61413

反応式

HRID 61413 の反応式
[CH2:1]=[CH:2][CH2:3][CH:4]1[C:8](=[O:9])[CH:7]=[CH:6][CH2:5]1.[C:10](=[O:20])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[NH2:11].O.O.O.O.O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[Bi+3].O>ClCCl>[CH2:3]([CH:4]1[C:8](=[O:9])[CH2:7][CH:6]([NH:11][C:10](=[O:20])[O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:5]1)[CH:2]=[CH2:1]

参加物

6

反応物 4

HCID 962WaterHCID 12136Benzyl carbamateHCID 160911Bismuth nitrate pentahydrateHCID 134445455-(Prop-2-en-1-yl)cyclopent-2-en-1-one

生成物 1

HCID 67513633Benzyl 3-allyl-4-oxocyclopentylcarbamate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 5-(propene-3-yl)cyclopent-2-enone (4.28 g, 35 mmol) in dichloromethane (15 mL) was treated with benzyl carbamate (10.6 g, 70 mmol) and bismuth trinitrate pentahydrate (2.2 g, 4.5 mmol), stirred rapidly for 18 h, then diluted with dichloromethane (50 mL). The mixture was filtered through Celite® (rinse with dichloromethane) and the filtrate added directly to a silica gel column (˜550 cc). Elution first with 3:2 petroleum ether/dichloromethane afforded recovered starting material (1.01 g), then 4:1 heptane/ethyl acetate gave the subject compound (4.54 g, 47.5% uncorrected yield) as a pale yellow oil. NMR (CDCl3): δ 7.28 (br s, 5 H), 5.55-5.70 (m, 1 H), 5.03 (br s, 2 H), 4.90-5.10 (m, 2 H), 4.75-4.90 (m, 1 H), 4.10-4.30 (m, 1 H), 2.40-2.80 (m, 2 H), 2.15-2.40 (m, 2 H), 1.85-2.15 (m, 3 H). MS (M+Na): 296.0; MS (M−H2O+1): 256.0 (no M+1 visible).

後処理

  1. filtrationThe mixture was filtered through Celite® (rinse with dichloromethane)
  2. additionthe filtrate added directly to a silica gel column (˜550 cc)
  3. washElution first with 3:2 petroleum ether/dichloromethane
  4. customafforded
  5. customrecovered
  6. custom4:1 heptane/ethyl acetate gave
  7. customthe subject compound (4.54 g, 47.5% uncorrected yield) as a pale yellow oil

出典と根拠

ORDレコード
ord-f2d56955c2bc4d60b6aa20377463e990
出典データセット
uspto-grants-2016_09
特許番号
US09440995B2

関連ノート

読み込み中…