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(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide → (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide

HRID 412636
Notes
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Reaction equation

HRID 412636 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][N:21](CC2C=CC=CC=2)[CH2:20]1)=[O:17]>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:11]([NH:10][CH2:15][CH3:14])[CH3:12].[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][C@H:11]1[C:16]([NH:18][C@@H:19]1[CH2:23][CH2:22][NH:21][CH2:20]1)=[O:17]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 1

HCID 57172017(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide

Product 2

HCID 8021DiethylamineHCID 57279632(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamideYield 4.1%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702
Ethanol
Solvent

Procedure

20% w/w Palladium hydroxide on carbon (12.5 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-1-benzylpyrrolidin-3-yl]-2-piperidinecarboxamide (62.5 mg) [see Example 1] in ethanol (10 ml). The reaction mixture was hydrogenated at 414 kPa (60 p.s.i.) for 56 hours, after which time the catalyst was filtered off and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, ethyl acetate:diethylamine to afford (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3R)-pyrrolidin-3-yl]-2-piperidinecarboxamide (1 mg) as an oil.

Workup

  1. filtrationafter which time the catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 95:5 changing to 90:10, by volume, ethyl acetate

Sources & evidence

ORD record
ord-8d8333426cc843e784b9fed7037fdbf9
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562964B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes