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

HRID 529549노트

반응식

HRID 529549 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-9f7832225c3a45bbb1469db306250068
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346852B2

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