Water → {1-Azabicyclo[3.3.1]nonan-5-yl}methanol

HRID 5363

반응식

HRID 5363 반응식
C([O:3][C:4]([C:6]12[CH2:14][N:10]([CH2:11][CH2:12][CH2:13]1)[CH2:9][CH2:8][CH2:7]2)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.O.[OH-].[Na+]>O1CCCC1>[N:10]12[CH2:14][C:6]([CH2:4][OH:3])([CH2:13][CH2:12][CH2:11]1)[CH2:7][CH2:8][CH2:9]2

참가 물질

6

반응물 4

HCID 962Water2회HCID 14798Sodium HydroxideHCID 19887573Ethyl 1-azabicyclo[3.3.1]nonane-5-carboxylateHCID 68718528lithium aluminium hydride THF

생성물 1

HCID 19795980{1-Azabicyclo[3.3.1]nonan-5-yl}methanol수율 98%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 1-azabicyclo[3.3.1]nonane-5-carboxylic acid ethyl ester (9.08 g, 46 mmol) in anhydrous tetrahydrofuran (25 mL) was added dropwise to a cooled (-10° C.) solution of 1.0N lithium aluminum hydride/tetrahydrofuran (50 mL, 50 mmol) in a 3-neck, 250-mL flask under nitrogen at a rate to keep the reaction temperature below, 5° C. The mixture was stirred for 15 minutes at room temperature, refluxed for 45 minutes, cooled (0° C.), and carefully treated dropwise with water (2 mL), 15% sodium hydroxide (2 mL), and water (6 mL). The suspension was filtered through Celite and the solid was washed with tetrahydrofuran. The filtrate was concentrated in vacuo to afford 6.99 g (98%) of colorless solid; mp 64.0°-65.5° C.

후처리

  1. custom5° C
  2. temperaturerefluxed for 45 minutes
  3. temperaturecooled (0° C.)
  4. filtrationThe suspension was filtered through Celite
  5. washthe solid was washed with tetrahydrofuran
  6. concentrationThe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-724adf2a51f8489d97c3c818d08a607f
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244907

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