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

HRID 2235913

反応式

HRID 2235913 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-99ced311783e4077b126db39288c8e33
出典データセット
uspto-grants-2010_05
特許番号
US07714004B2

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