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Benzyl Bromide → Ethyl {cis-1-benzyl-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate

HRID 602446
ノート
印刷プレビュー

反応式

HRID 602446 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][NH:13][C@@H:12]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[CH2:30](Br)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(#N)C>[CH2:30]([N:13]1[CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH2:11][C@@H:12]1[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 86624143Ethyl {cis-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate

生成物 1

HCID 86624144Ethyl {cis-1-benzyl-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate収率 82.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a stirred solution of ethyl {cis-5-[(tert-butoxycarbonyl)amino]piperidin-2-yl}acetate (2.25 g, 7.86 mmol, step 5 of Example 1), N,N-diisopropylethylamine (1.12 g, 8.64 mmol) in acetonitrile (45 mL) was added benzyl bromide (1.48 g, 8.64 mmol) at room temperature. After stirring at room temperature for 28 h, the mixture was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate (250 mL). The organic solution was washed with water (100 mL×3), brine (50 mL), dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1) to give 2.44 g (82%) of the title compound as a colorless oil.

後処理

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate (250 mL)
  3. washThe organic solution was washed with water (100 mL×3), brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-de12a02a7d07448bb2c597b2804e663f
出典データセット
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07906532B2

反応ノート

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