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2-Naphthalenecarboxaldehyde → Ethyl 2-(5-naphthalen-2-ylmethylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyrimidine-5-carboxylate

HRID 2079817
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HRID 2079817 반응식
[CH2:1]1[CH:5]2[CH2:6][NH:7][CH2:8][CH:4]2[CH2:3][N:2]1[C:9]1[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=1.[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[CH:30]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22][C:21]=1[CH2:30][N:7]1[CH2:6][CH:5]2[CH2:1][N:2]([C:9]3[N:14]=[CH:13][C:12]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][N:10]=3)[CH2:3][CH:4]2[CH2:8]1
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반응물 4

HCID 62012-NaphthalenecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 59367682Ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylate

생성물 1

HCID 59367601Ethyl 2-(5-naphthalen-2-ylmethylhexahydropyrrolo[3,4-c]pyrrol-2(1H)-yl)pyrimidine-5-carboxylate수율 99%

시약·촉매·용매

2
HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

To a solution of ethyl 2-hexahydropyrrolo[3,4-c]pyrrol-2(1H)-ylpyrimidine-5-carboxylate (0.187 g, 0.71 mmol) in DCE (2 ml) was added 2-naphthaldehyde (0.205 g, 1.31 mmol) and sodium triacetoxyborohydride (0.274 g, 1.25 mmol). The mixture was stirred for 3 h, then poured into DCM (100 ml). Sat. NaHCO3 (100 ml) was added, and extracted with further DCM (100 ml). The combined organic extracts were dried (MgSO4), concentrated and purified by flash column chromatography to yield the title compound (0.266 g, 99%). 1H NMR (300 MHz, CDCl3) δ: 1.39 (3H, t, J=6.9 Hz), 2.59 (2H, d, J=6.9 Hz), 2.73-2.90 (2H, m), 2.94-3.10 (2H, m), 3.67 (2H, d, J=11.7 Hz), 3.82 (2H, s), 3.90 (2H, dd, J=8.1, 12 Hz), 4.37 (2H, q, J=7.2 Hz), 7.41-7.43 (3H, m), 7.74 (1H, s), 7.76-7.89 (3H, m), 8.88 (2H, s).

후처리

  1. extractionextracted with further DCM (100 ml)
  2. dry with materialThe combined organic extracts were dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography

출처 및 근거

ORD 기록
ord-e06411dd06744f6babea7f125f036faf
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07932246B2

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