تفاعل #88529

معادلة التفاعل

(1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid hydrogen chloride

lithium tetrahydroaluminate

→

(1R,3S,4S)-2-azabicyclo[2.2.1]heptan-3-ylmethanol

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was quenched with a few drops of water
2. 2
   workup.ADDITIONdiluted with diethyl ether (50 mL) and tetrahydrofuran (25 mL)
3. 3
   workup.ADDITIONThe reaction mixture was basified to a pH of ˜11 by the addition of potassium hydroxide pellets
4. 4
   workup.STIRRINGstirred vigorously for 30 minutes
5. 5
   ترشيحThe reaction mixture was filtered over sodium sulfate
6. 6
   تركيزconcentrated in vacuo
7. 7
   workup.DISSOLUTIONredissolved in methylene chloride (10 mL)
8. 8
   تجفيفdried once more over sodium sulfate
9. 9
   ترشيحfiltered
10. 10
    تركيزconcentrated in vacuo
11. 11
    أخرىto afford a yellow crystalline solid, which
12. 12
    أخرىwas used in the next step without any further purification (400 mg, 100%)

الإجراء التجريبي

To a slurry of (1R,3S,4S)-2-azabicyclo[2.2.1]heptane-3-carboxylic acid hydrogen chloride (500 mg, 3 mmol) in tetrahydrofuran (4.6 mL) was added lithium tetrahydroaluminate (1N solution in tetrahydrofuran, 5.7 mL, 6 mmol) dropwise over 10 minutes. The reaction mixture was stirred overnight at ambient temperature under an atmosphere of nitrogen. The reaction was quenched with a few drops of water, diluted with diethyl ether (50 mL) and tetrahydrofuran (25 mL). The reaction mixture was basified to a pH of ˜11 by the addition of potassium hydroxide pellets and then stirred vigorously for 30 minutes. The reaction mixture was filtered over sodium sulfate, concentrated in vacuo, redissolved in methylene chloride (10 mL), dried once more over sodium sulfate, filtered, and concentrated in vacuo to afford a yellow crystalline solid, which was used in the next step without any further purification (400 mg, 100%).

المصدر