Triphenyl phosphite → (S)-methyl 6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazine-3-carboxylate

HRID 716250

反応式

HRID 716250 の反応式
C[O:2][C:3]([C@@H:5]1[CH2:10][CH2:9][CH2:8][CH2:7][N:6]1[C:11]1[C:20]([N+:21]([O-])=O)=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][N:12]=1)=O.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1.[H][H]>ClCCl.N.O[V](=O)=O.[Pt]>[O:2]=[C:3]1[NH:21][C:20]2[CH:19]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=[N:12][C:11]=2[N:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C@@H:5]12

参加物

7

反応物 3

HCID 7540Triphenyl phosphiteHCID 58324510(S)-methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinateHCID 178418361HCID 178418361、化合物

生成物 1

HCID 58324495(S)-methyl 6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazine-3-carboxylate収率 89%

試薬・触媒・溶媒 3

HCID 23939Platinum触媒HCID 62684Ammonium metavanadate [UN2859] [Poison]触媒HCID 6344Dichloromethane溶媒2 回

実験手順

In a bomb hydroginator, (S)-methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinate (1.95 g, 6.03 mmol), triphenyl phosphite (0.019 ml, 0.060 mmol), ammonium vanadate (0.056 g, 0.483 mmol) and platinum (5% on carbon, 0.235 g, 0.060 mmol) were mixed in dichloromethane (Volume: 30.2 ml) to give a suspension. The bomb was sealed and pressurized to 110 psi with hydrogen gas. The reaction was stirred at 110 psi 16 h, depressurized, diluted with DCM (100 mL) and refluxed 10 minutes. The hot mixture was filtered through celite and washed with DCM (50 mL). The filtrate was concentrated in vacuo to yield 1.4 g (89%) of the product as a white solid and used without further purification. [M+H] calc'd for C13H15N3O3, 262. found, 262.

後処理

  1. customto give a suspension
  2. customThe bomb was sealed
  3. temperaturerefluxed 10 minutes
  4. filtrationThe hot mixture was filtered through celite
  5. washwashed with DCM (50 mL)
  6. concentrationThe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-95f3c4b5b04e413aaf77fc4f2e8a02c1
出典データセット
uspto-grants-2015_11
特許番号
US09187497B2

関連ノート

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