Benzyl Bromide → HCID 18686046、化合物

HRID 278281ノート

反応式

HRID 278281 の反応式
[OH:1][CH2:2][C@@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][C:5](=[CH2:15])[CH2:4]1.[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[H-].[Na+]>CN(C=O)C.CCOCC>[CH2:16]([O:1][CH2:2][C@@H:3]1[C@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)[CH2:6][C:5](=[CH2:15])[CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18686049HCID 18686049、化合物

生成物 1

HCID 18686046HCID 18686046、化合物収率 47.4%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 3-(S)-(hydroxymethyl)-4-(R)-(3-fluorophenyl)-1-methylenecyclopentane (3.11 g, 16.5 mmol) from Example 65, Step C in DMF (100 mL) was added benzyl bromide (4.24 g, 24.8 mmol) and then sodium hydride (60% in mineral oil, 0.73 g, 18.2 mmol) portionwise over 5 min. The reaction was stirred at rt for 16 h, then diluted with ether (100 mL) and quenched slowly into aq. sodium bicarbonate (200 mL). The layers were separated and the aqueous was extracted with ether. The organic layers were washed 3× with water, then brine, dried over sodium sulfate and concentrated. The residue (7 g) was purified by FC using 0.5-1% ethyl acetate in hexanes to afford the title compound (2.32 g).

後処理

  1. customquenched slowly into aq. sodium bicarbonate (200 mL)
  2. customThe layers were separated
  3. extractionthe aqueous was extracted with ether
  4. washThe organic layers were washed 3× with water
  5. dry with materialbrine, dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe residue (7 g) was purified by FC

出典と根拠

ORDレコード
ord-8326f02bdadf4d7cbd80e2b7830649bc
出典データセット
uspto-grants-2002_03
特許番号
US06358979B1

反応ノート

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