Tetrahydrofuran → Benzyl 4-(4-(tert-butyldimethylsilyloxy)butyl)-4-cyanopiperidine-1-carboxylate

HRID 597842

反応式

HRID 597842 の反応式
[C:1]([CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1)#[N:2].CCCC.I[Si:24]([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[CH2:41]1[CH2:45][O:44][CH2:43][CH2:42]1>>[Si:24]([O:44][CH2:43][CH2:42][CH2:41][CH2:45][C:3]1([C:1]#[N:2])[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[O:10])[CH2:5][CH2:4]1)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 2733832Lithium HexamethyldisilazideHCID 22028286Benzyl 4-cyanopiperidine-1-carboxylateHCID 86616696HCID 86616696、化合物

生成物 1

HCID 67270654Benzyl 4-(4-(tert-butyldimethylsilyloxy)butyl)-4-cyanopiperidine-1-carboxylate収率 67%

実験手順

To a stirred solution of benzyl 4-cyanopiperidine-1-carboxylate (10 g, 41 mmol) and iodo-tert-butyldimethylsilane butane (12.6 mL, 49 mmol) in THF (80 mL) cooled to −78° C. was added LiHMDS (50 mL, 50 mmol, 1M in THF) dropwise over 30 min. The resulting mixture was stirred while gradually warming to room temperature for 18 h. After quenching with water, the organic phase was diluted with EtOAc and washed with water, brine and dried (Na2SO4). After concentration, the residue was purified by flash chromatography (10% to 20% EtOAc/hexane) to give the title compound as yellow oil (11.88 g, 67% yield). 1H NMR (300 MHz, CDCl3) δ: 7.34-7.28 (5H, m), 5.09 (2H, s), 4.17 (2H, bs), 3.59 (2H, t, J=5.3 Hz), 3.07 (2H, bs), 1.89 (2H, d, J=13.2 Hz), 1.53 (6H, bs), 1.43-1.34 (2H, m), 0.85 (9H, s), 0.01 (6H, s). LCMS (M+H): 431.20.

後処理

  1. customAfter quenching with water
  2. additionthe organic phase was diluted with EtOAc
  3. washwashed with water, brine
  4. dry with materialdried (Na2SO4)
  5. concentrationAfter concentration
  6. customthe residue was purified by flash chromatography (10% to 20% EtOAc/hexane)

出典と根拠

ORDレコード
ord-f009d28e78c04276a7da1ea5be3ef8c9
出典データセット
uspto-grants-2011_03
特許番号
US07897593B2

関連ノート

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