1-Pentadecene → tert-Butyl-(2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate

HRID 2200835

반응식

HRID 2200835 반응식
[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C@H:11]([O:14][CH2:15][O:16][CH3:17])[CH:12]=[CH2:13])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH2:19]=[CH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31]CC>C(Cl)Cl.CC1C=C(C)C(N2C(=[Ru](Cl)(Cl)=CC3C=CC=CC=3)N(C3C(C)=CC(C)=CC=3C)CC2)=C(C)C=1.C1CCC(P(C2CCCCC2)C2CCCCC2)CC1>[C:1]([O:5][C:6](=[O:18])[NH:7][C@H:8]([C@H:11]([O:14][CH2:15][O:16][CH3:17])/[CH:12]=[CH:13]/[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH3:19])[CH2:9][OH:10])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 259131-PentadeceneHCID 86670891tert-Butyl-(2S,3R)-1-hydroxy-3-(methoxymethoxy)pent-4-en-2-yl-carbamate

생성물 1

HCID 44551220tert-Butyl-(2S,3R,4E)-1-hydroxy-3-(methoxymethoxy)octadec-4-en-2-yl-carbamate수율 72%

시약·촉매·용매 2

HCID 11147261(1,3-Dimesitylimidazolidin-2-ylidene)(tricyclohexylphosphine)benzylidene ruthenium dichloride촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of alcohol 6 (230 mg, 0.88 mmol) in CH2Cl2 (8 mL) was added 1-pentadecene (741 mg, 3.52 mmol). The solution was degassed twice using N2 (2×10 min). To the reaction mixture was added benzylidene[1,3-bis(2,4,6-trimethyl -phenyl)-2-imidazolidinylidene]dichloro-(tricyclohexylphosphine)ruthenium catalyst (22.4 mg, 0.026 mmol) at rt under N2. After the reaction mixture was stirred for 4 h under reflux, the solvent was removed and the product was purified by chromatography (hexane/EtOAc 4:1) to afford 7 (280 mg, 72%): Rf0.45 (EtOAc/hexane 1:3); 1H NMR (CDCl3) δ 0.88 (t, 3H, J=7.0 Hz), 1.25 (m, 24H), 1.44 (m, 9H), 2.06 (q, 2H, J=7.7 Hz), 2.89 (d, 1H, J=5.2 Hz), 3.38 (s, 3H), 3.67 (m, 2H), 3.94 (dt, 1H, J=3.2, 11.1 Hz), 4.22 (dd, 1H, J=5.0, 7.6 Hz), 4.53 (d, 1H, J=6.6 Hz), 4.67 (d, 1H, J=6.6 Hz), 5.26 (d, 1H,J =7.6 Hz), 5.36 (dd, 1H, J=8.0, 15.4 Hz), 5.75 (dt, 1H, J=6.6, 14.6 Hz); 13C NMR (CDCl3) δ 14.1, 22.7, 28.4, 29.0, 29.1, 29.3, 29.4, 29.6, 29.7, 31.9, 32.3, 54.9, 55.6, 62.3, 76.1, 78.3, 79.4, 93.8, 125.9, 136.9, 155.9; ESI-HRMS [M+Na]+C25H49NO5Na calcd for m/z 466.3508, found 466.3514.

후처리

  1. customThe solution was degassed twice using N2 (2×10 min)
  2. temperatureunder reflux
  3. customthe solvent was removed
  4. customthe product was purified by chromatography (hexane/EtOAc 4:1)

출처 및 근거

ORD 기록
ord-e5c7041e3d8b42fa82a7a13a6cf011ca
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359389B2

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