تفاعل #2266936

ord-12b0a9a8055343bc98d56cc7369d4b23

معادلة التفاعل

CCOC(=O)C1(CC)CCN(C(=O)OC(C)(C)C)CC1
1-tert-butyl 4-ethyl 4-ethylpiperidine-1,4-dicarboxylate
O=C(O)C(F)(F)F
trifluoro acetic acid
O=C([O-])O.[Na+]
NaHCO3
CCOC(=O)C1(CC)CCNCC1
title compound
المردود 95.8%
CCOC(=O)C1(CC)CCNCC1
ethyl 4-ethylpiperidine-4-carboxylate
المردود 95.8%

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    أخرىthe reaction at room temperature for about 6 hours
  2. 2
    أخرىUpon completion of the reaction (monitored by TLC)
  3. 3
    استخلاصextracted with DCM
  4. 4
    تجفيفthe organic layer was dried over Na2SO4
  5. 5
    تركيزconcentrated under reduced pressure

الإجراء التجريبي

To a stirred solution of 1-tert-butyl 4-ethyl 4-ethylpiperidine-1,4-dicarboxylate (above step 2, 4.5 g, 12.96 mmol) in 50 ml DCM was cooled to 0° C. After ten minutes trifluoro acetic acid (6.0 g) was added and stirred the reaction at room temperature for about 6 hours. Upon completion of the reaction (monitored by TLC), the reaction mixture was neutralized with saturated NaHCO3 and extracted with DCM, the organic layer was dried over Na2SO4 and concentrated under reduced pressure to furnish the title compound (2.3 g) as a light yellow liquid. 1H NMR (300 MHz, CDCl3): 1.19-1.24 (t, 3H); 1.48-1.58 (m, 2H); 2.14-2.18 (m, 2H); 2.64-2.73 (m, 2H); 2.86 (s, 2H); 3.01-3.07 (m, 4H); 4.10-4.17 (m, 2H); 7.07-7.10 (m, 2H); 7.24-7.30 (m, 3H); ES Mass: 186 (100%), [M+1].

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09067966B2uspto-grants-2015_06