Triphenylphosphine → Ethyl{(1S)-5-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetate

HRID 46033노트

반응식

HRID 46033 반응식
C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:38]([O:40][C:41](=[O:53])[CH2:42][C@H:43]1[C:51]2[C:46](=[CH:47][C:48]([OH:52])=[CH:49][CH:50]=2)[CH2:45][CH2:44]1)[CH3:39].[CH3:54][C:55]1[N:56]=[C:57]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[O:58][C:59]=1[CH2:60][CH2:61]O>C1COCC1.C(Cl)Cl>[CH3:54][C:55]1[N:56]=[C:57]([C:63]2[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=2)[O:58][C:59]=1[CH2:60][CH2:61][O:52][C:48]1[CH:47]=[C:46]2[C:51](=[CH:50][CH:49]=1)[C@H:43]([CH2:42][C:41]([O:40][CH2:38][CH3:39])=[O:53])[CH2:44][CH2:45]2

참가 물질

7

반응물 4

HCID 11776Triphenylphosphine2회HCID 730421,1'-(Azodicarbonyl)dipiperidine2회HCID 16110404ethyl 2-[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetateHCID 219427522-(4-Methyl-2-phenyl-1,3-oxazol-5-yl)ethanol

생성물 1

HCID 60128085Ethyl{(1S)-5-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetate수율 73%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

ADDP (0.205 g, 0.81 mmol) was added to a mixture of PPh3 (0.212 g, 0.81 mmol), ethyl[(1S)-5-hydroxy-2,3-dihydro-1H-inden-1-yl]acetate (0.107 g, 0.49 mmol), and 2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethanol (step 4, Example 51, 0.110 g, 0.54 mmol) in THF (5 mL). The reaction was stirred overnight at rt, and additional ADDP (0.136 g, 0.54 mmol) and PPh3 (0.141 g, 0.54 mmol) were added with CH2Cl2 (5 mL). The solution was stirred for 24 hours at rt and filtered. The filtrate was evaporated and the resulting mixture was purified by Biotage using a gradient 0 to 50%. EtOAc/hexane. Gave ethyl {(1S)-5-[2-(4-methyl-2-phenyl-1,3-oxazol-5-yl)ethoxy]-2,3-dihydro-1H-inden-1-yl}acetate (0.145 g, 66% yield) as yellowish oil. ES-MS m/z 406.2 ((MH)+); HPLC RT (min.) 3.89; 1H NMR (Acetone-d6) δ 7.85-7.82 (m, 2H), 7.36-7.30 (m, 3H), 6.94 (d, 1H), 6.65 (s, 1H), 6.60-6.55 (m, 1H), 4.10 (t, 2H), 3.98 (q, 2H), 3.31-3.27 (m, 1H), 3.03 (t, 2H), 3.27-2.51 (m, 3H), 2.24-2.14 (m, 2H), 2.18 (s, 3H), 1.58-1.53 (m, 1H), 1.08 (t, 3H).

후처리

  1. stirringThe solution was stirred for 24 hours at rt
  2. filtrationfiltered
  3. customThe filtrate was evaporated
  4. customthe resulting mixture was purified by Biotage

출처 및 근거

ORD 기록
ord-a4546baa493c43e18eca7a9d89b25d83
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541618B2

반응 노트

불러오는 중…