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

HRID 535085Notes

Reaction equation

HRID 535085 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-147f950d07c74dbaa44cf28e1d6bde62
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

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