Dimethylformamide → Methyl (2s,3s,5s)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

HRID 61477Notes

Reaction equation

HRID 61477 reaction equation
[C:1]([O:5][C@@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([OH:14])=O)[C@@H:8]([C:15]([O:17][CH3:18])=[O:16])[CH2:7]1)([CH3:4])([CH3:3])[CH3:2].[C:19]1([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CN(C)C=O.C(N(CC)C(C)C)(C)C>>[C:1]([O:5][C@@H:6]1[CH2:11][NH:10][C@H:9]([C:12]([N:28]2[CH2:29][CH2:30][N:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:26][CH2:27]2)=[O:14])[C@@H:8]([C:15]([O:17][CH3:18])=[O:16])[CH2:7]1)([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67304647HCID 67304647, compound

Product 1

HCID 67304371Methyl (2s,3s,5s)-5-tert-butoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

Procedure

To a mixture of (2S,3S,5S)-5-tert-butoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid (43.0 mg, 0.000166 mol), 1-phenyl-piperazine (0.03166 mL, 0.0002073 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.09168 g, 0.0002073 mol) in N,N-dimethylformamide (0.40 mL, 0.0052 mol) was added N,N-diisopropylethylamine (0.03611 mL, 0.0002073 mol). The reaction was stirred at rt for 2 h, then quenched with water. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried and concentrated to dry. The residue was used directly in next step. MS (ESI): (M+H)+=404.2.

Workup

  1. customquenched with water
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry

Sources & evidence

ORD record
ord-32763dc847ed41fd80b3e599ccbaa4bb
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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