1,2-Dichloroethane → HCID 57888800, Verbindung

HRID 1016145Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1016145
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][NH:11][CH2:10][C:9]2([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[C:17]([O:21][C:22]([N:24]([CH3:32])[C@H:25]([CH:29]([CH3:31])[CH3:30])[C:26](O)=[O:27])=[O:23])([CH3:20])([CH3:19])[CH3:18].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(N(CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([OH:16])[CH2:13][CH2:12][N:11]([C:26](=[O:27])[C@H:25]([N:24]([CH3:32])[C:22](=[O:23])[O:21][C:17]([CH3:19])([CH3:18])[CH3:20])[CH:29]([CH3:31])[CH3:30])[CH2:10][C:9]2([CH3:14])[CH3:15])=[CH:4][CH:3]=1

Komponenten

7

Edukt 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 7018800Boc-N-methyl-D-ValineHCID 18437142(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol

Produkt 1

HCID 57888800HCID 57888800, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(S)-4-(4-chlorophenyl)-3,3-dimethylpiperidin-4-ol (100 mg, 0.417 mmol), (R)-2-(tert-butoxycarbonyl(methyl)amino)-3-methylbutanoic acid (116 mg, 0.501 mmol), HOBT (77 mg, 0.501 mmol), EDC (96 mg, 0.501 mmol) and triethylamine (0.116 mL, 0.834 mmol) were mixed in methylene chloride (3 mL) at 25° C. with stirring. The reaction was stirred for 20 hours then washed with sat'd sodium bicarbonate. The methylene chloride layer was dried over sodium sulfate and concentrated in vacuo to give a white glass which was purified over silica gel (9:1 to 3:1 to 1:1 Hexanes/EtOAc) to obtain tert-butyl (R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl(methyl)carbamate (190 mg, 0.417 mmol, 100% yield) as a white glass. MS found: (M+H)+=453.15.

Aufarbeitung

  1. stirringThe reaction was stirred for 20 hours
  2. washthen washed with sat'd sodium bicarbonate
  3. dry with materialThe methylene chloride layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give a white glass which
  6. customwas purified over silica gel (9:1 to 3:1 to 1:1 Hexanes/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-38f3d1c819a44e8b9b5ba22fae4d6b1f
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07985861B2

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