Dimethylformamide → Methyl (2s,3s,5s)-2-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-3-carboxylate

HRID 61463

Reaktionsgleichung

Reaktionsgleichung von HRID 61463
[CH3:1][O:2][C:3]([C@H:5]1[CH2:10][C@H:9]([O:11][C:12]([N:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])[CH2:8][NH:7][C@@H:6]1[C:19]([OH:21])=O)=[O:4].[C:22]1([C:28]2[CH2:29][CH2:30][NH:31][CH2:32][CH:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=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:22]1([C:28]2[CH2:33][CH2:32][N:31]([C:19]([C@@H:6]3[C@@H:5]([C:3]([O:2][CH3:1])=[O:4])[CH2:10][C@H:9]([O:11][C:12]([N:14]4[CH2:15][CH2:16][CH2:17][CH2:18]4)=[O:13])[CH2:8][NH:7]3)=[O:21])[CH2:30][CH:29]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 825531,2,3,6-Tetrahydro-4-phenylpyridineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 67304698(2s,3s,5s)-3-(Methoxycarbonyl)-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2-carboxylic acid

Produkt 1

HCID 67304271Methyl (2s,3s,5s)-2-[(4-phenyl-3,6-dihydropyridin-1(2h)-yl)carbonyl]-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-3-carboxylate

Versuchsvorschrift

To a mixture of (2S,3S,5S)-3-(methoxycarbonyl)-5-[(pyrrolidin-1-ylcarbonyl)oxy]piperidine-2-carboxylic acid (90.1 mg, 0.000300 mol) and 4-phenyl-1,2,3,6-tetrahydropyridine (64.6 mg, 0.000330 mol) HCl salt, benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (146 mg, 0.000330 mol) in N,N-dimethylformamide (0.44 mL, 0.0057 mol) was added N,N-diisopropylethylamine (0.115 mL, 0.000660 mol) at rt. The mixture was stirred at rt overnight, then quenched with aq. sodium bicarbonate. After separation of the organic layers, the aq. layer was extracted with EtOAc. The combined organic layers were washed with brine, dried, and concentrated to dry. The crude material was used directly in next step.

Aufarbeitung

  1. customquenched with aq. sodium bicarbonate
  2. customAfter separation of the organic layers
  3. extractionthe aq. layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customto dry

Quellen und Nachweise

ORD-Eintrag
ord-8f429a7246e44e3396caab35b3332f8a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440958B2

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