tert-Butyl (6-methylpyridin-2-yl)carbamate → HCID 59858004、化合物

HRID 1671614ノート

反応式

HRID 1671614 の反応式
[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([CH3:19])=O.[C:20](=[O:22])=O.[Li][CH2:24][CH2:25][CH2:26][CH3:27]>C1COCC1>[C:1]([O:5][C:6](=[O:15])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][CH:13]2[CH:20]([OH:22])[CH2:6][N:7]([CH2:16][C:17]3[CH:19]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:8]2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 11367776tert-Butyl (6-methylpyridin-2-yl)carbamateHCID 18522661Acetone cardiceHCID 178418339Butyllithium

生成物 1

HCID 59858004HCID 59858004、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of (6-methyl-pyridin-2-yl)-carbamic acid tert-butyl ester I-1 (0.00625 mol) in 10 mL THF was cooled in a −78° C. bath (acetone/dry ice). n-BuLi (1.6 M in hexanes, 0.0125 mol) was added during 15 min. under N2. The color of solution was changed from colorless to orange. Then the cooling bath was removed. After 45 min stirring at room temperature, the color solution was changed into dark red. The solution was then returned to the −78° C. bath. 3-Benzyl-6-oxa-3-aza-bicyclo[3.1.0]hexane I-2 (0.005 mol) in 10 mL THF was added during 1 h. After 2 h, the cooling bath was removed. The solution was stirred for 2 h more at room temperature. The reaction was quenched by the addition of ice-cold water (50 ml). The mixture was extracted with CH2Cl2 (30 ml×3). The combined organic layers were washed with brine and dried over anhydrous MgSO4. The solvent was removed in vacuo and the residue was purified by column chromatography (silica gel, CH2Cl2: MeOH, 9:1) (90%).

後処理

  1. customThen the cooling bath was removed
  2. customwas then returned to the −78° C. bath
  3. addition(0.005 mol) in 10 mL THF was added during 1 h
  4. waitAfter 2 h
  5. customthe cooling bath was removed
  6. stirringThe solution was stirred for 2 h more at room temperature
  7. customThe reaction was quenched by the addition of ice-cold water (50 ml)
  8. extractionThe mixture was extracted with CH2Cl2 (30 ml×3)
  9. washThe combined organic layers were washed with brine
  10. dry with materialdried over anhydrous MgSO4
  11. customThe solvent was removed in vacuo
  12. customthe residue was purified by column chromatography (silica gel, CH2Cl2: MeOH, 9:1) (90%)

出典と根拠

ORDレコード
ord-a45f754c28504915b7e91dbd703ae4b7
出典データセット
uspto-grants-2011_08
特許番号
US07994326B2

反応ノート

読み込み中…