Triphenylphosphine → (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

HRID 1182662노트

반응식

HRID 1182662 반응식
O[C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][C:8]1[N:13]([CH3:14])[C:12](=[O:15])[CH:11]=[CH:10][N:9]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C1(C)C=CC=CC=1>[CH3:14][N:13]1[C:12](=[O:15])[CH:11]=[CH:10][N:9]2[C:8]1=[N:7][C@@H:3]1[CH2:4][CH2:5][CH2:6][C@@H:2]12

참가 물질

6

반응물 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 673709162-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one

생성물 1

HCID 67379018(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one수율 92%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-((1R,2R)-2-hydroxycyclopentylamino)-3-methylpyrimidin-4(3H)-one (130 mg, 0.62 mmol) in anhydrous THF (2 mL) is added triphenylphosphine (163 mg, 0.62 mmol). Five minutes later, diethyl azodicarboxylate (DEAD, 0.45 mL, 0.93 mmol) in toluene is added dropwise. The mixture is stirred at room temperature for 2 hours. Solvent is removed under vacuum, the residue is treated with 0.02 N HCl (40 mL). The precipitate is filtered off, and the filtrate is washed with CH2Cl2. The aqueous phase is evaporated to dryness under high vacuum to give product as solids (108 mg, yield 92%), which is used for the next reaction without further purification. MS (ESI) m/z 192.1 [M+H]+.

후처리

  1. customSolvent is removed under vacuum
  2. additionthe residue is treated with 0.02 N HCl (40 mL)
  3. filtrationThe precipitate is filtered off
  4. washthe filtrate is washed with CH2Cl2
  5. customThe aqueous phase is evaporated to dryness under high vacuum

출처 및 근거

ORD 기록
ord-eabe886922f44740a0e2dee11993f525
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08664207B2

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