Potassium Carbonate → 3-(1-Boc-2-(s)-pyrrolidinylmethoxy)-6-chloro-5-methylpyridine

HRID 2305196노트

반응식

HRID 2305196 반응식
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH3:12])[C:8]([Cl:11])=[N:9][CH:10]=1)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+].[C:19](C1(C)C=CC=C[C@]1(C)S([O-])(=O)=O)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[NH:38]1C[CH2:41][CH2:40][CH2:39]1>CO>[C:19]([N:38]1[CH2:39][CH2:40][CH2:41][C@H:2]1[CH2:1][O:4][C:5]1[CH:10]=[N:9][C:8]([Cl:11])=[C:7]([CH3:12])[CH:6]=1)([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 218288696-Chloro-5-methylpyridin-3-yl acetateHCID 1317220211-BOC-2-(S)-methyltoluenesulfonate pyrrolidine

생성물 1

HCID 229618403-(1-Boc-2-(s)-pyrrolidinylmethoxy)-6-chloro-5-methylpyridine수율 46.2%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of 5-acetoxy-2-chloro-3-methylpyridine (1.80 g, 8.9 mmol) in MeOH (5 mL) was added potassium carbonate (1.4 g, 10.1 mmol). The reaction mixture was allowed to stir at room temperature for 2.5 h. Solvent was evaporated. The residue was then dissolved in DMF, and 1-BOC-2-(S)-methyltoluenesulfonate-pyrrolidine (2.0 g, 5.63 mmol) from a above was added. The reaction mixture was stirred at 60° C. for 16 h. Solvent was evaporated. The residue was chromatographed (silica gel; hexane/EtOAc, 10:1 to 3:1) to afford an oil (850 mg, 30%): 1H NMR δ 1.47 (s, 9H), 1.80-2.00 (m, 2H), 2.00-2.08 (m, 2H), 2.34 (s, 3H), 3.24-3.44 (m, 2H), 3.92 (m, 1H), 4.02-4.20 (m, 2H), 7.16 (m, 1H), 7.92 (d, 1H, J=2.5 Hz); MS (CI/NH3) m/z 227 (M+H)+.

후처리

  1. customSolvent was evaporated
  2. dissolutionThe residue was then dissolved in DMF
  3. stirringThe reaction mixture was stirred at 60° C. for 16 h
  4. customSolvent was evaporated
  5. customThe residue was chromatographed (silica gel; hexane/EtOAc, 10:1 to 3:1)

출처 및 근거

ORD 기록
ord-8717caf9aec548e6a5723da4c462e510
출처 데이터셋
uspto-grants-2002_08
특허 번호
US06437138B1

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