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

HRID 365912ノート

反応式

HRID 365912 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-63fd7c10c4ba43279e2579e8e88b92b3
出典データセット
uspto-grants-2000_10
特許番号
US06127386

反応ノート

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