Triethylamine → HCID 178453892, Verbindung

HRID 72848

Reaktionsgleichung

Reaktionsgleichung von HRID 72848
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([CH:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[C:6]=2[CH:16]=1.[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:29][CH2:28][C@H:27]([CH2:30][CH:31]=O)[CH2:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:17]([O:21][C:22](=[O:33])[NH:23][C@H:24]1[CH2:25][CH2:26][C@H:27]([CH2:30][CH2:31][N:13]2[CH2:12][CH2:11][CH:10]([C:7]3[C:6]4[CH:16]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[O:9][N:8]=3)[CH2:15][CH2:14]2)[CH2:28][CH2:29]1)([CH3:20])([CH3:19])[CH3:18]

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 27947555-Fluoro-3-(4-piperidinyl)-1,2-benzisoxazoleHCID 5049666Sodium triacetoxyborohydrideHCID 178453924HCID 178453924, Verbindung2×

Produkt 1

HCID 178453892HCID 178453892, VerbindungAusbeute 102 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

A mixture of 5-fluoro-3-(4-piperidinyl)-1,2-benzisoxazole (1.3 g, 5 mmol), trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (example 1, intermediate C) (1.6 g, 6 mmol), triethylamine (0.64 mL, 5 mmol) in 1,2 dichloroethane (27 mL) was stirred for 4 h at room temperature and sodium triacetoxyborohydride (1.9 g, 9 mmol) was added slowly and the resulting solution was stirred for 12 hours until the TLC indicated completion of the reaction. The mixture was filtrated and concentrated to dryness and purified with column chromatography on silica gel using CH2Cl2—CH2Cl2/MeOH (1-9:1). The product fractions were concentrated to give 2.3 g (5.1 mmol, 100% yield) of a off-white solid. MS (m/e): 446.3 (M+H+).

Aufarbeitung

  1. stirringthe resulting solution was stirred for 12 hours until the TLC
  2. customcompletion of the reaction
  3. filtrationThe mixture was filtrated
  4. concentrationconcentrated to dryness
  5. custompurified with column chromatography on silica gel
  6. concentrationThe product fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-376f96ff0f514fed88ddc6e5c17bd469
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829029B2

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