Triphenylphosphine → ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate

HRID 603446

반응식

HRID 603446 반응식
[OH:1][CH2:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[C@H:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][CH2:8]2.[CH3:20][C:21]1[C:26](O)=[CH:25][CH:24]=[C:23]([CH3:28])[N:22]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1CCN(C(N=NC(N2CCCCC2)=O)=O)CC1>C1COCC1>[CH3:20][C:21]1[C:26]([O:1][CH2:2][CH2:3][O:4][C:5]2[CH:6]=[C:7]3[C:11](=[CH:12][CH:13]=2)[C@H:10]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:9][CH2:8]3)=[CH:25][CH:24]=[C:23]([CH3:28])[N:22]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 707322,6-Dimethyl-3-pyridinolHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 59300449ethyl [(1S)-5-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-1-yl]acetate

생성물 1

HCID 59300516ethyl ((1S)-5-{2-[(2,6-dimethyl-3-pyridinyl)oxy]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl [(1S)-5-(2-hydroxyethoxy)-2,3-dihydro-1H-inden-1-yl]acetate (Example 249, 50.0 mg, 0.19 mmol) and 2,6-dimethylpyridin-3-ol (46.6 mg, 0.38 mmol) in THF (1.5 mL) were added PPh3 (99.2 mg, 0.38 mmol) and ADDP (95.5 mg, 0.38 mmol). The reaction mixture was vigorously stirred at rt for 24 h, and then directly applied to a silica gel column for purification (1:1 hexanes/EtOAc) to give the product (58.9 mg, 84%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 1.29 (t, 3H) 1.72-1.81 (m, 1H), 2.36-2.2.44 (m, 2H), 2.45 (s, 3H), 2.47 (s, 3H), 2.73 (dd, 1H) 2.82-2.92 (m, 2H), 3.52-3.56 (m, 1H) 4.19 (q, 2H), 4.26-4.33 (m, 4H), 6.75 (d, 1H), 6.82 (s, 1H) 6.92 (d, 1H), 7.05 (d, 1H), 7.08 (d, 1H).

후처리

  1. customdirectly applied to a silica gel column for purification (1:1 hexanes/EtOAc)

출처 및 근거

ORD 기록
ord-c4f2660a6f224899a0f40533804a2b6a
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906653B2

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