تفاعل #89717

معادلة التفاعل

Lithium hexamethyldisilazide

1-benzyl 4-methyl(2S)-2-[benzyl((2S)-2-(1-ethoxyethoxy)-3-[(4-methylphenyl)sulfonyl]oxypropyl)amino]succinate

toluene

→

product

المردود 69.9%

2-benzyl 3-methyl(2S,3S,5R)-1-benzyl-5-(1-ethoxyethoxy)piperidine-2,3-dicarboxylate

المردود 69.9%

المذيبات

tetrahydrofuran

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةto warm up to −20 Celsius
2. 2
   workup.STIRRINGstirred at −20 Celsius for 3 h
3. 3
   أخرىAfter quenched with aq ammonium chloride
4. 4
   استخلاصthe mixture was extracted with ethyl acetate
5. 5
   غسيلThe combined organic layers were washed with brine
6. 6
   أخرىdried
7. 7
   تركيزconcentrated
8. 8
   أخرىto dry
9. 9
   غسيلeluting with 0 to 20% EtOAc in hexane

الإجراء التجريبي

To a solution of 1-benzyl 4-methyl(2S)-2-[benzyl((2S)-2-(1-ethoxyethoxy)-3-[(4-methylphenyl)sulfonyl]oxypropyl)amino]succinate (35.7 g, 0.0569 mol) in a mixture of tetrahydrofuran (95.5 mL, 1.18 mol) and toluene (490 mL, 4.6 mol) at −78 Celsius was was added 1.00 M of Lithium hexamethyldisilazide in tetrahydrofuran (68.2 mL). The reaction was stirred at −78 Celsius overnight then allowed to warm up to −20 Celsius and stirred at −20 Celsius for 3 h. After quenched with aq ammonium chloride, the mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to dry. The residue was applied on silica gel column, eluting with 0 to 20% EtOAc in hexane, to afford the product (18.1 g, 69.9%). MS (ESI): (M+H)+=456.2. The corresponding diastereoisomer was also obtained (4.52 g, 17.5%).

المصدر