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

HRID 365912노트

반응식

HRID 365912 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 tenperature 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-63fd7c10c4ba43279e2579e8e88b92b3
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06127386

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