تفاعل #89736

ord-68fccff24262489a9e2b463e97495487

معادلة التفاعل

CN1C[C@@H](OC(=O)N2CCCC2)C[C@H](C(=O)NO)[C@H]1C(=O)N1CC=C(c2ccccc2)CC1
(3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate
[H][H]
hydrogen
→
CN1C[C@@H](OC(=O)N2CCCC2)C[C@H](C(=O)NO)[C@H]1C(=O)N1CCC(c2ccccc2)CC1
product
المردود 100.0%
CN1C[C@@H](OC(=O)N2CCCC2)C[C@H](C(=O)NO)[C@H]1C(=O)N1CCC(c2ccccc2)CC1
(3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenylpiperidin-1-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate
المردود 100.0%

المتفاعلات

CN1C[C@@H](OC(=O)N2CCCC2)C[C@H](C(=O)NO)[C@H]1C(=O)N1CC=C(c2ccccc2)CC1
(3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate
[H][H]
hydrogen

الكواشف

O=S(=O)([O-])[O-].[Ba+2].[Pd]
Pd BaSO4

المذيبات

CO
MeOH

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    ترشيحAfter filtered off the catalyst
  2. 2
    ترشيحthe filtration
  3. 3
    تركيزwas concentrated
  4. 4
    أخرىto dry

الإجراء التجريبي

A solution of (3S,5S,6S)-5-[(hydroxyamino)carbonyl]-1-methyl-6-[(4-phenyl-3,6-dihydropyridin-1(2H)-yl)carbonyl]piperidin-3-yl pyrrolidine-1-carboxylate (5.0 mg, 0.000011 mol) TFA salt in 1 mL of MeOH was hydrogenated in the presence of 5% Pd/BaSO4, under a balloon pressure of hydrogen, for 2 h. After filtered off the catalyst, the filtration was concentrated to dry to give the product (5.0 mg, 100%). MS (ESI): (M+H)+=459.15.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09440958B2uspto-grants-2016_09