(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate → (R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate

HRID 529549ノート

反応式

HRID 529549 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:18])[CH2:10]/[CH:11]=[CH:12]/[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>C(O)C.[Pd]>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:18])[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 86706226(R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 86706227(R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate収率 100%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

A suspension of (R,E)-ethyl 5-(tert-butoxycarbonylamino)hex-2-enoate (1.70 g, 6.61 mmol) and 5% Pd/C (350 mg) in ethanol (35 mL) was vigorously stirred under the atmosphere of hydrogen balloon for 1.5 hr. The reaction mixture was filtered and the filtrate were concentrated to give (R)-ethyl 5-(tert-butoxycarbonylamino)hexanoate (1.71 g, 6.58 mmol, 100% yield) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.34 (s, 1H), 4.12 (q, J=7.1 Hz, 2H), 3.66 (s, 1H), 2.31 (td, J=7.5, 1.6 Hz, 2H), 1.75-1.57 (m, 2H), 1.51-1.38 (m, 2H), 1.44 (s, 9H), 1.25 (t, J=7.1 Hz, 3H), 1.12 (d, J=6.6 Hz, 3H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate were concentrated

出典と根拠

ORDレコード
ord-9f7832225c3a45bbb1469db306250068
出典データセット
uspto-grants-2016_05
特許番号
US09346852B2

反応ノート

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