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2-Aminopropanol → (2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-hydroxypropyl)-2-piperidinecarboxamide

HRID 397689
Notes
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Reaction equation

HRID 397689 reaction equation
O.[OH:2][C:3]1[C:11]2[N:10]=NNC=2C=C[CH:4]=1.CN1CCOCC1.[F:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[C:35]([OH:37])=O)(=[O:28])=[O:27])=[CH:22][CH:21]=1.NC(C)CO>C(OCC)(=O)C>[F:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([N:29]2[CH2:34][CH2:33][CH2:32][CH2:31][C@H:30]2[C:35]([NH:10][CH2:11][CH:3]([OH:2])[CH3:4])=[O:37])(=[O:27])=[O:28])=[CH:24][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 51262-AminopropanolHCID 79724-MethylmorpholineHCID 768662(2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 57047664(2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-hydroxypropyl)-2-piperidinecarboxamideYield 83.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Hydroxybenzotriazole hydrate (297 mg), (3-dimethylminopropyl)-3-ethylcarbodiimide (421 mg) and N-methylmorpholine (241 ml) were added to a solution of (2S)-1-[(4-fluorophenyl)sulfonyl]-2-piperidinecarboxylic acid (575 mg) [see Preparation 38]. The reaction mixture was stirred for 15 mins, then 2-aminopropanol (170 ml) was added and stirring continued for 18 hrs at room temperature. The mixture was then diluted with ethyl acetate and washed with 2M aqueous hydrochloric acid, saturated sodium hydrogen carbonate and water. The organic layer was separated, dried over magnesium sulphate and the solvent removed under reduced pressure to afford (2S)-1-[(4-fluorophenyl)sulfonyl]-N2-(2-hydroxypropyl)-2-piperidinecarboxamide (555 mg) as an oil.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hrs at room temperature
  3. washwashed with 2M aqueous hydrochloric acid, saturated sodium hydrogen carbonate and water
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b831f661cb7943779ed51201f42e180d
Source dataset
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06610707B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes