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

HRID 222142

반응식

HRID 222142 반응식
[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(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20].C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[CH3:1][N:2]1[CH:6]2[CH2:7][CH:8]([O:10][S:19]([CH3:18])(=[O:21])=[O:20])[CH2:9][CH:3]1[CH2:4][CH2:5]2

참가 물질

7

반응물 4

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chloride

생성물 1

HCID 1419518-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonate수율 78.1%

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

반응 조건

온도
20 °C

실험 절차

Tropine (50 g) and triethylamine (60 mL, 43.56 g) in dichloromethane (1 L) were cooled to −10° C. Methane sulphonyl chloride (36 mL, 53.28 g) in dichloromethane (0.2 L) was added over 1 h at −5+/−2° C. After 0.5 h a solution of potassium carbonate (150 g) in water (0.4 L) was added and the mixture warmed to 20° C. The phases were separated and the aqueous phase extracted with further dichloromethane (1×0.2 L). The combined dichloromethane solution was concentrated by distillation collecting 1 L. n-Heptane (0.875 L) was added and the mixture stirred for 0.5 h. The solution was decanted off and then concentrated by distillation at 610 to 650 mbar until a solution temperature of 63° C. was reached. The solution was cooled to 0° C. with crystallization occurring during the cooling. The mixture was stirred for 1 h, the product isolated by filtration, washed and dried at <30° C. to give the title compound (60.62 g, 78.1%).

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase extracted with further dichloromethane (1×0.2 L)
  3. concentrationThe combined dichloromethane solution was concentrated by distillation
  4. customcollecting 1 L
  5. additionn-Heptane (0.875 L) was added
  6. customThe solution was decanted off
  7. concentrationconcentrated by distillation at 610 to 650 mbar until a solution temperature of 63° C.
  8. temperatureThe solution was cooled to 0° C. with crystallization
  9. stirringThe mixture was stirred for 1 h
  10. customthe product isolated by filtration
  11. washwashed
  12. customdried at <30° C.

출처 및 근거

ORD 기록
ord-3f02659a912c4bbdaf5ea287d5bb31b1
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207191B2

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