[4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester → [4-(4-Cyanophenyl)butyl]carbamic acid tert-butyl ester

HRID 217946

反応式

HRID 217946 の反応式
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C.C1COCC1>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]#[N:19])=[CH:16][CH:17]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 2

HCID 67364707[4-(4-Cyanophenyl)but-3-ynyl]carbamic acid tert-butyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 67366079[4-(4-Cyanophenyl)butyl]carbamic acid tert-butyl ester収率 87.3%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

A suspension of [4-(4-cyanophenyl)but-3-ynyl]carbamic acid tert-butyl ester 56 (5.2 g, 19.2 mmol) and 10% palladium on carbon (2.5 g, wet) in ethanol/THF (30 mL, 1:1) was stirred overnight under 1 atmosphere of hydrogen. After purging with nitrogen, the reaction mixture was suction filtered through a pad of Celite. The solvent was removed from the filtrate by evaporation. The residue was chromatographed on silica gel, eluting with methylene chloride/ethyl acetate (30:1), to afford the pure product 57 (4.6 g, 87%) as an oil. 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.51 (m, 2H), 1.65 (m, 2H), 2.69 (t, 2H), 3.14 (m, 2H), 4.52 (br s, 1H), 7.27 (d, 2H), 7.56 (d, 2H).

後処理

  1. customAfter purging with nitrogen
  2. filtrationfiltered through a pad of Celite
  3. customThe solvent was removed from the filtrate by evaporation
  4. customThe residue was chromatographed on silica gel
  5. washeluting with methylene chloride/ethyl acetate (30:1)

出典と根拠

ORDレコード
ord-05b270af3eb4433e935d656b41e9d67d
出典データセット
uspto-grants-2012_06
特許番号
US08198286B2

関連ノート

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