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Triethylamine → Methyl (2s,4r)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-2-carboxylate

HRID 389193
ノート
印刷プレビュー

反応式

HRID 389193 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[NH:8][C:7](=[O:14])[CH:6]=[C:5]2[O:15][C@H:16]1[CH2:20][N:19](C(OC(C)(C)C)=O)[C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]1.[CH:32]([B-](F)(F)F)=[CH2:33].[K+].CCN(CC)CC>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[CH3:13][O:12][C:11]1[CH:10]=[C:9]2[C:4]([C:5]([O:15][C@H:16]3[CH2:20][NH:19][C@H:18]([C:28]([O:30][CH3:31])=[O:29])[CH2:17]3)=[CH:6][C:7](=[O:14])[NH:8]2)=[CH:3][C:2]=1[CH:32]=[CH2:33]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 59279885HCID 59279885、化合物

生成物 1

HCID 59279894Methyl (2s,4r)-4-[(7-methoxy-2-oxo-6-vinyl-1,2-dihydroquinolin-4-yl)oxy]pyrrolidine-2-carboxylate収率 127.9%

試薬・触媒・溶媒 2

HCID 178418807HCID 178418807、化合物触媒
HCID 702Ethanol溶媒

実験手順

To a solution of the product from Step 2 (2.26 g, 4.54 mmol) in EtOH (45.4 mL) was added potassium vinyltrifluoroborate (0.913 g, 6.82 mmol), Et3N (0.950 mL, 6.82 mmol), and PdCl2(dppf)-DCM adduct (0.186 g, 0.227 mmol). The reaction mixture was then heated to reflux for 1 hour, cooled to RT; the volatiles were evaporated in vacuo; and the residue partitioned between EtOAc and water. The organic phase was dried over MgSO4, and the solvent was removed in vacuo. The crude material was purified on silica (gradient elution, 0-5% MeOH/DCM) to yield 2.0 g of the title compound. LRMS ESI+ ((M-Boc)+H)+ 345.3.

後処理

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 1 hour
  3. customthe volatiles were evaporated in vacuo
  4. customand the residue partitioned between EtOAc and water
  5. dry with materialThe organic phase was dried over MgSO4
  6. customthe solvent was removed in vacuo
  7. customThe crude material was purified on silica (gradient elution, 0-5% MeOH/DCM)

出典と根拠

ORDレコード
ord-fbe57c6449e6473b9b6e68ef195e8818
出典データセット
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08377874B2

反応ノート

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