Dimethyl Carbonate → Methyl N-(4-methylpyridin-3-yl)carbamate

HRID 1257624

反応式

HRID 1257624 の反応式
CC(C)([O-])C.[K+].[NH2:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[CH3:14].[C:15](=O)([O:18]C)[O:16][CH3:17]>C1COCC1>[CH3:17][O:16][C:15](=[O:18])[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[CH:12][C:13]=1[CH3:14]

参加物

5

反応物 3

HCID 12021Dimethyl CarbonateHCID 1379353-Amino-4-picolineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 11672725Methyl N-(4-methylpyridin-3-yl)carbamate収率 62%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of potassium tert-butoxide (32.8 g, 277 mmol) in THF (250 mL) at 0° C. was treated with 3-amino-4-methylpyridine (10.0 g, 92.5 mmol) and the resulting mixture stirred for 30 minutes before dimethyl carbonate (11.7 mL, 139 mmol) was added. The mixture was stirred for 30 minutes then quenched with water and extracted with ethyl acetate. The combined organic phases were washed with brine then dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (DCM) then triturated with diethyl ether to afford 9.42 g (62%) of (4-methyl-pyridin-3-yl)-carbamic acid methyl ester. LCMS (Method B, ESI): RT=0.40 min, m+H=167.4; 1H NMR (400 MHz, CDCl3) δ: 8.86 (s, 1H), 8.28 (d, 1H), 7.12-7.12 (m, 1H), 6.45 (s, 1H), 3.80 (s, 3H), 2.28 (s, 3H).

後処理

  1. additionwas added
  2. customthen quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with brine
  5. dry with materialthen dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe resulting residue was purified by column chromatography on silica gel (DCM)
  8. customthen triturated with diethyl ether

出典と根拠

ORDレコード
ord-9d5cd1ef7c374d5e89d959be79315aa3
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

関連ノート

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