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

HRID 535081Notes

Reaction equation

HRID 535081 reaction equation
[CH3:1][O:2][C@@H:3]1[CH2:8][NH:7][C@H:6]([C:9]([OH:11])=O)[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:4]1.[C:16]1([N:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=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>>[CH3:1][O:2][C@@H:3]1[CH2:8][NH:7][C@H:6]([C:9]([N:25]2[CH2:26][CH2:27][N:22]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][CH2:24]2)=[O:11])[C@@H:5]([C:12]([O:14][CH3:15])=[O:13])[CH2:4]1

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 70961-PhenylpiperazineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67305316(2s,3s,5s)-5-Methoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid

Product 1

HCID 67304478Methyl (2s,3s,5s)-5-methoxy-2-[(4-phenylpiperazin-1-yl)carbonyl]piperidine-3-carboxylate

Procedure

To a mixture of (2S,3S,5S)-5-methoxy-3-(methoxycarbonyl)piperidine-2-carboxylic acid (14.0 mg, 0.0000644 mol), 1-phenyl-piperazine (0.01231 mL, 8.056E-5 mol) and benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (35.63 mg, 8.056E-5 mol) in N,N-dimethylformamide (0.20 mL, 0.0026 mol)was added N,N-diisopropylethylamine (0.01403 mL, 8.056E-5 mol). The mixture was stirred at rt for 2 h. After quenched with water, the mixture was extracted with ethyl acetate. The combine organic layers were washed with brine, dried and concentrated to dry. The residue was used directly in next step without further purification. MS (ESI): (M+H)+=362.1.

Workup

  1. customAfter quenched with water
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combine organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto dry
  7. customThe residue was used directly in next step without further purification

Sources & evidence

ORD record
ord-cd155ee9f6e4401a89580aba540cc78e
Source dataset
uspto-grants-2014_10
Patent number
US08853243B2

Reaction notes

Loading…