8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → 8-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonate

HRID 222143

反応式

HRID 222143 の反応式
[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([OH:10])[CH2:9][CH:3]1[CH2:4][CH2:5]2.C(N(C(C)C)CC)(C)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O.CCCCCCC>[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([O:10][S:21]([CH3:20])(=[O:23])=[O:22])[CH2:9][CH:3]1[CH2:4][CH2:5]2

参加物

8

反応物 4

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 81531Diisopropylethylamine

生成物 1

HCID 1419518-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonate収率 88.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6344Dichloromethane溶媒2 回HCID 8900Heptane溶媒

反応条件

温度
20 °C

実験手順

Tropine (50 g) and diisopropylethylamine (48.05 g) in dichloromethane (0.5 L) were cooled to −10° C. Methane sulphonyl chloride (44.7 g) in dichloromethane (0.125 L) was added over 0.75 h at <−5° C. After 0.5 h a solution of potassium carbonate (75 g) in water (0.2 L) was added and the mixture warmed to 20° C. The phases were separated and the dichloromethane solution concentrated by distillation under reduced pressure at <20° C. to leave a residue whereby the dichloromethane content was 51% w/w. Heptane (0.05 L) was added and the solution cooled to 0° C. to crystallize the title compound. Further heptane (0.45 L) was added and the mixture kept under vacuum (350 mbar) at 20-25° C. until the dichloromethane content was 8% w/w. The mixture was cooled to 0° C. and stirred for 1 h. The product was isolated by filtration, washed and dried at <30° C. to give the title compound (68.5 g, 88.1%).

後処理

  1. customThe phases were separated
  2. concentrationthe dichloromethane solution concentrated by distillation under reduced pressure at <20° C.
  3. customto leave a residue whereby the dichloromethane content
  4. temperaturethe solution cooled to 0° C.
  5. customto crystallize the title compound
  6. additionFurther heptane (0.45 L) was added
  7. customkept under vacuum (350 mbar) at 20-25° C. until the dichloromethane content
  8. temperatureThe mixture was cooled to 0° C.
  9. customThe product was isolated by filtration
  10. washwashed
  11. customdried at <30° C.

出典と根拠

ORDレコード
ord-79acaea70afd430ca372e42da7e5e71a
出典データセット
uspto-grants-2012_06
特許番号
US08207191B2

関連ノート

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