Sodium hydride → 5-Ethynyl-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine

HRID 724906

반응식

HRID 724906 반응식
O[C:2](C)(C#C)[CH2:3][C:4]1[CH:5]=[C:6]([CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]=[N:8][CH:9]=1.[H-].[Na+].C1(C)C=CC=CC=1.CC(C)=O>C1(C)C=CC=CC=1>[C:3]([C:4]1[CH:5]=[C:6]([CH:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH:7]=[N:8][CH:9]=1)#[CH:2]

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 196943235-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridineHCID 20247278Toluene acetone

생성물 1

HCID 196943285-Ethynyl-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine수율 61.2%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
25 °C

실험 절차

5-(2-Hydroxy-2-methyl-3-butynyl)-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine (495 mg, 1.5 mmol) was dissolved in toluene (30 mL) and catalytic sodium hydride (10 mg) was added. The solution was heated until several milliliters of toluene-acetone mixture was removed by distillation. The mixture was cooled to 25° C. and water (20 mL) and ethyl acetate (40 mL) were added. The organic phase was separated and the aqueous layer extracted with ethyl acetate (2×40 mL) and the combined organic extracts were washed with brine (20 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by silica gel column chromatography with ethyl acetate:hexane (1:3) as eluant to afford 5-ethynyl-3-(1-tert-butyloxycarbonyl-2-pyrrolidinyl)pyridine as an oil (250 mg, 61%). LRMS (EI) m/e 217 (M+ +H--isobutylene), 216 (M+ --isobutylene); 1H NMR (CDCl3, 300 MHz): δ 8.59 (b-s, 1H), 8.42 (d, J=1.5 Hz, 1H), 7.59 (b-s, 1H), 4.94 (b-m, 0.5H), 4.77 (b-m, 0.5H), 3.64 (b-m, 2H), 3.21 (s, 1H), 2.39 (m, 1H), 1.75-2.0 (b-m, 3H), 1.46 (s, 3H), 1.21 (s, 6H).

후처리

  1. customwas removed by distillation
  2. additionwater (20 mL) and ethyl acetate (40 mL) were added
  3. customThe organic phase was separated
  4. extractionthe aqueous layer extracted with ethyl acetate (2×40 mL)
  5. washthe combined organic extracts were washed with brine (20 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel column chromatography with ethyl acetate:hexane (1:3) as eluant

출처 및 근거

ORD 기록
ord-11c11ff3dc8048f18aef3c9e7a9da015
출처 데이터셋
uspto-grants-1998_01
특허 번호
US05705512

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