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 69623

반응식

HRID 69623 반응식
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

참가 물질

7

반응물 3

HCID 7540Triphenyl phosphiteHCID 58324510(S)-methyl 6-(2-(methoxycarbonyl)piperidin-1-yl)-5-nitronicotinateHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 23939Platinum촉매HCID 62684Ammonium metavanadate [UN2859] [Poison]촉매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5ca4146512848e68549ed74dd7bf83e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822470B2

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