تفاعل #440598

ord-0aab0a77f3bc42828e79e7062857db87

معادلة التفاعل

C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
cinchonidine
O=C(O)CC(C(=O)O)c1c[nH]c2ccccc12
racemic indole-3-succinic acid
→
C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12.O=C(O)C[C@H](C(=O)O)c1c[nH]c2ccccc12
(S)-indole-3-succinic acid cinchonidine
المردود 13.1%

المتفاعلات

C=C[C@H]1CN2CC[C@H]1C[C@H]2[C@H](O)c1ccnc2ccccc12
cinchonidine
O=C(O)CC(C(=O)O)c1c[nH]c2ccccc12
racemic indole-3-succinic acid

الكواشف

لا شيء

المذيبات

CCO
ethanol

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةwas heated on a steam bath
  2. 2
    workup.DISSOLUTIONdissolved
  3. 3
    أخرىthe white precipitate formed
  4. 4
    أخرىwas collected
  5. 5
    غسيلwashed with ether
  6. 6
    أخرىAfter 11 recrystallizations from 96% ethanol and one solution of 96% ethanol
  7. 7
    تجفيفmethanol, 80:20 by volume, and drying

الإجراء التجريبي

A mixture of 1.26 g (4.29 mmole) of cinchonidine and 1.00 g (4.29 mmole) of racemic indole-3-succinic acid in 10 mL of 96% ethanol was heated on a steam bath with magnetic stirring until all of the solid dissolved. The solution was cooled slowly to room temperature, and the white precipitate formed was collected and washed with ether. After 11 recrystallizations from 96% ethanol and one solution of 96% ethanol:methanol, 80:20 by volume, and drying, colorless fine needles of (S)-indole-3-succinic acid-cinchonidine salt was obtained. 0.296 g, yield: 13.1%, ee: 99.3%. Mp: 196-198° C. (with gas evolution). Elemental analysis: Calculated for C31H33N3O55: C=70.57%, H=6.30%, N=7.96% Found: C=70.00%; H=6.42%; N=7.84%. IR: 3500-2900, 1592, 1460 cm-1. By fractional removal of (S)-indole-3-succinic acid salt, followed by rotary evaporation of the solvent and recrystallization (supra vide), the (R)-indole-3-succinic acid-cinchonidine salt was obtained.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US06753297B2uspto-grants-2004_06