Allyltributylstannane → 5-Allyl-3-(1-boc-2-(s)-pyrrolidinylmethoxy)pyridine

HRID 365895ノート

反応式

HRID 365895 の反応式
Br[C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[N:6][CH:7]=1.[CH2:22]([Sn](CCCC)(CCCC)CCCC)[CH:23]=[CH2:24]>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:24]([C:2]1[CH:3]=[C:4]([O:8][CH2:9][C@@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:5]=[N:6][CH:7]=1)[CH:23]=[CH2:22]

参加物

5

反応物 2

HCID 90628AllyltributylstannaneHCID 15480235(S)-2-((5-Bromopyridin-3-yloxy)methyl)pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 229618865-Allyl-3-(1-boc-2-(s)-pyrrolidinylmethoxy)pyridine収率 346%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

5-Bromo-3-(1-BOC-2-(S)-pyrrolidinylmethoxy)pyridine (948 mg, 2.66 mmol) in toluene (10 mL) was added tetrakis(triphenylphosphine)palladium (15 mg) and allyltributyltin (0.18 mL, 0.56 mmol). The mixture was stirred and refluxed for two days. Solvent was evaporated and the residue was chromatographed (silica gel; hexane/EtOAc, 5:1 to 1:1) to afford an oil (617 mg, 73%): 1H NMR (CDCl3, 300 MHz) δ 1.96 (m, 1H), 2.04-2.20 (m, 2H), 2.28 (m, 1H), 3.42 (t, 2H, J=7.0 Hz), 3.54 (d, 2H, J=7.0 Hz), 4.14 (m, 1H), 4.31 (dd, 1H, J=8.0, 10.5 Hz), 4.51 (dd, 1H, J=3.5, 10.5 Hz), 5.12-5.22 (m, 2H), 6.02 (m, 1H), 7.77 (s, 1H), 8.23 (s, 1H), 8.30 (d, 1H, J=2.5 Hz); MS (CI/NH3) m/e 219 (M+H)+.

後処理

  1. temperaturerefluxed for two days
  2. customSolvent was evaporated
  3. customthe residue was chromatographed (silica gel; hexane/EtOAc, 5:1 to 1:1)

出典と根拠

ORDレコード
ord-2dc0a4ab74464afe947823a8b7063ad0
出典データセット
uspto-grants-2000_10
特許番号
US06127386

反応ノート

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