Sodium hydride → rac-ethyl (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylate

HRID 2174211

반응식

HRID 2174211 반응식
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[NH2:9][C:10]1[CH:15]=[CH:14][C:13](/[CH:16]=[CH:17]/[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][CH:11]=1>CS(C)=O>[NH2:9][C:10]1[CH:11]=[CH:12][C:13]([C@@H:16]2[CH2:4][C@H:17]2[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14][CH:15]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 736317Ethyl 4-aminocinnamate

생성물 1

HCID 68767952rac-ethyl (1R,2R)-2-(4-aminophenyl)cyclopropane-1-carboxylate

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

To a suspension of sodium hydride (36 mg, 0.89 mmol) in DMSO (2 mL) was added the solid trimethyl sulfoxonium iodide (185 mg, 1.05 mmol). The mixture was stirred for 25 min before a solution of ethyl (E)-3-(4-aminophenyl)prop-2-enoate (100 mg, 0.52 mmol) in DMSO (2 mL) was added quickly at RT. The mixture was left to stir overnight. The bulk mixture was quenched with NH4Cl (sat.) and the mixture diluted with water and EtOAc. The layers were separated and the aqueous layer extracted into EtOAc (3×30 mL). The organic fractions were combined, dried with brine then MgSO4 and the solvent removed. Flash chromatography on silica gel, eluting with 20-50% ethyl acetate gradient in n-heptane, gave ethyl (1R,2R)-2-(4-aminophenyl)cyclopropanecarboxylate, 70 mg. 1H NMR (400 MHz, CDCl3) δ 6.96-6.89 (m, 2H), 6.68-6.61 (m, 2H), 4.17 (q, J=7.1 Hz, 2H), 2.44 (ddd, J=9.2, 6.6, 4.2 Hz, 1H), 1.80 (ddd, J=8.4, 5.2, 4.2 Hz, 1H), 1.53 (ddd, J=9.2, 5.2, 4.5 Hz, 1H), 1.28 (t, J=7.1 Hz, 3H), 1.24 (ddd, J=8.3, 6.6, 4.5 Hz, 1H).

후처리

  1. additionwas added quickly at RT
  2. waitThe mixture was left
  3. customThe bulk mixture was quenched with NH4Cl (sat.)
  4. additionthe mixture diluted with water and EtOAc
  5. customThe layers were separated
  6. extractionthe aqueous layer extracted into EtOAc (3×30 mL)
  7. dry with materialdried with brine
  8. customMgSO4 and the solvent removed
  9. washFlash chromatography on silica gel, eluting with 20-50% ethyl acetate gradient in n-heptane

출처 및 근거

ORD 기록
ord-e5828ed443d141db9fd38cdc33533811
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09060515B2

연결된 노트

불러오는 중…