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Triphenylphosphine → 1-tert-butyl 2-[2-(trimethylsilyl)ethyl] (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate

HRID 1360094
ノート
印刷プレビュー

反応式

HRID 1360094 の反応式
[OH:1][C@@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:3]1.[C:23]1([C:29]2[NH:30][C:31]3[C:36]([C:37](=O)[CH:38]=2)=[CH:35][C:34]([CH:40]=[CH2:41])=[CH:33][CH:32]=3)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:23]1([C:29]2[CH:38]=[C:37]([O:1][C@H:2]3[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:12])([CH3:13])[CH3:11])=[O:8])[C@H:4]([C:14]([O:16][CH2:17][CH2:18][Si:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:3]3)[C:36]3[C:31](=[CH:32][CH:33]=[C:34]([CH:40]=[CH2:41])[CH:35]=3)[N:30]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 11776Triphenylphosphine2 回HCID 5462977Diethyl azodicarboxylate2 回HCID 576171082-phenyl-6-vinylquinolin-4(1H)-oneHCID 576171281-tert-butyl 2-[2-(trimethylsilyl)ethyl] (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate

生成物 1

HCID 576171271-tert-butyl 2-[2-(trimethylsilyl)ethyl] (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate
収率 50.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of 1-tert-butyl 2-[2-(trimethylsilyl)ethyl] (2S,4S)-4-hydroxypyrrolidine-1,2-dicarboxylate 3 (1.0 g, 3.02 mmol) in THF (30 mL) was added 2-phenyl-6-vinylquinolin-4(1H)-one 2 (0.78 g, 3.17 mmol) and PPh3 (1.19 g, 4.52 mmol). The flask was then cooled to 0° C. and diethylazodicarboxylate (0.713 mL, 4.52 mmol) was added slowly. The mixture was then warmed to RT and stirred overnight (16 h). At this time, the starting material to product ratio was 2:1. The reaction was re-cooled to 0° C., and additional PPh3 (1.19 g, 4.52 mmol) and diethylazodicarboxylate (0.713 mL, 4.52 mmol) were added. After stirring for an additional 19 h, only a small amount of starting material remained. Silica gel was then added to the reaction and the mixture was filtered through silica gel with EtOAc as the eluent. The crude mixture was then purified on silica (5-40% EtOAc/hexanes) to yield 0.85 g (50% yield) of 1-tert-butyl 2-[2-(trimethylsilyl)ethyl] (2S,4R)-4-[(2-phenyl-6-vinylquinolin-4-yl)oxy]pyrrolidine-1,2-dicarboxylate 5. 1H NMR (500 MHz, CDCl3) ppm: mixture of amide rotamers: 8.43 (m, 1H), 8.13-8.09 (m, 2H), 7.92 and 7.91 (2 br s, 2H), 7.56 (m, 3H), 7.12 and 7.11 (2 br s, 1H), 6.92 (br dd, J=17.5 Hz, 10.5 Hz, 1H), 6.02 (d, J=17.5 Hz, 1H), 5.58 (d, J=10.5 Hz, 1H), 5.53 and 5.49 (2 br s, 1H), 4.64 and 4.54 (2 app t, J=7.5 Hz, 1H), 4.27 (app t, J=7 Hz, 2H), 4.07 (m, 1.5H), 3.89 (br d, J=13 Hz, 0.5H), 2.81 (m, 1H), 2.55 (m, 1H), 1.47 and 1.45 (2 s, 9H), 1.04 (m, 2H), 0.07 and 0.06 (2 s, 9H). LRMS (CI, [M+H]) Calc'd=561.4. found=561.4. HRMS (APCI, [M+H]+) Calc'd for C32H41N2O5Si: 561.2779. found: 561.2749.

後処理

  1. temperatureThe mixture was then warmed to RT
  2. temperatureThe reaction was re-cooled to 0° C.
  3. stirringAfter stirring for an additional 19 h
  4. additionSilica gel was then added to the reaction
  5. filtrationthe mixture was filtered through silica gel with EtOAc as the eluent
  6. customThe crude mixture was then purified on silica (5-40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-785b08fdf0ee415ebd659854baa1f9a9
出典データセット
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07879797B2

反応ノート

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