Triphenylphosphine → Methyl 5-bromo-6-oxo-1-(3-phenylcyclopentyl)-1,6-dihydropyridine-3-carboxylate

HRID 253091노트

반응식

HRID 253091 반응식
[Br:1][C:2]1[C:7](=[O:8])[NH:6][CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1.[C:13]1([CH:19]2[CH2:23][CH2:22][CH:21](O)[CH2:20]2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.C(OC(=O)C)C>[Br:1][C:2]1[C:7](=[O:8])[N:6]([CH:22]2[CH2:21][CH2:20][CH:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:23]2)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[CH:3]=1

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 2756203-Phenylcyclopentan-1-olHCID 2764315Methyl 5-bromo-6-hydroxynicotinate

생성물 1

HCID 66844665Methyl 5-bromo-6-oxo-1-(3-phenylcyclopentyl)-1,6-dihydropyridine-3-carboxylate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of methyl 5-bromo-6-oxo-1,6-dihydropyridine-3-carboxylate (1.6 g, 6.8 mmol), 3-phenylcyclopentanol (1.32 g, 8.15 mmol) and triphenylphosphine (2.7 g, 10.2 mmol) in dry THF (15 mL) was slowly added diethyl azodicarboxylate (1.8 g, 10.2 mmol) at RT. The resulting yellow solution was stirred at room temperature for 17 h. The mixture was diluted in ethylacetate, washed with water, brine, dried over MgSO4, and chromatographed on silica gel using hexanes to 3:1 hexanes:ethylacetate, to afford the title compound. MS m/z: 376 (M+1).

후처리

  1. customat RT
  2. washwashed with water, brine
  3. dry with materialdried over MgSO4
  4. customchromatographed on silica gel

출처 및 근거

ORD 기록
ord-23391fb9e5f04c8db0331fa34b411ec5
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872009B2

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