Water → {1-Azabicyclo[3.2.1]octan-5-yl}methanol

HRID 5362

반응식

HRID 5362 반응식
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.C([O:14][C:15]([C:17]12[CH2:24][N:21]([CH2:22][CH2:23]1)[CH2:20][CH2:19][CH2:18]2)=O)C.O.[OH-].[Na+]>O1CCCC1>[N:21]12[CH2:24][C:17]([CH2:15][OH:14])([CH2:23][CH2:22]1)[CH2:18][CH2:19][CH2:20]2

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 15663615Ethyl 1-azabicyclo[3.2.1]octane-5-carboxylateHCID 68718528lithium aluminium hydride THF

생성물 1

HCID 19795992{1-Azabicyclo[3.2.1]octan-5-yl}methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A cooled (0° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (55 mL, 55 mmol) under nitrogen was treated dropwise with a solution of 1-azabicyclo[3.2.1]octane-5-carboxylic acid ethyl ester (9.17 g, 50 mmol) in anhydrous tetrahydrofuran (20 mL), stirred for 30 minutes at room temperature, refluxed for one hour, and cooled (0° C.). In sequence, water (2.1 mL), 15% sodium hydroxide solution (2.1 mL) and water (6.3 mL) were carefully added dropwise, and the mixture was filtered through Celite (the solid was washed with tetrahydrofuran) and concentrated in vacuo to afford 6.50 g (92%) of viscous, colorless oil, which can be used as is or can be solidified on cooling; mp 44°-47° C.

후처리

  1. temperaturerefluxed for one hour
  2. temperaturecooled (0° C.)
  3. filtrationthe mixture was filtered through Celite (the solid
  4. washwas washed with tetrahydrofuran) and
  5. concentrationconcentrated in vacuo
  6. customto afford 6.50 g (92%) of viscous, colorless oil, which
  7. temperatureon cooling

출처 및 근거

ORD 기록
ord-3f6f7292f4214dacbbc44e42e9963d38
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244907

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