Triethylamine → (S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carboxylic acid ethyl ester

HRID 1423118Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423118
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:36]([O:38][CH2:39][CH3:40])=[O:37].C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[CH2:39]([O:38][C:36]([N:13]1[CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9][C@@H:8]1[CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:37])[CH3:40]

Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

Produkt 1

HCID 23627686(S)-2-Benzyl-4-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine-1-carboxylic acid ethyl esterAusbeute 34,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (73 mg, 0.2 mmol) in THF (0.5 mL) at room temperature was treated with triethylamine (28 μL, 0.2 mmol) followed by ethyl chloroformate (19 μL, 0.2 mmol). The reaction mixture was stirred for 2 h then diluted with EtOAc (2 mL) followed by a saturated aqueous NaHCO3 solution (1 mL). The organic phase was isolated and further washed with an additional portion of a saturated aqueous NaHCO3 solution (1 mL) followed by a brine solution (1 mL). The organic component was dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 10% then 30% EtOAc/hexane as eluant to afford the title compound as an oil (30 mg, 34%). 1H NMR (CDCl3) 7.34-7.22 (m, 5H), 6.77 (d, J=8.6, 1H), 6.47 (s, 1H), 6.39 (dd, J=8.6, 2.4, 1H), 4.72-4.69 (m, 1H), 4.40 (br s, 1H), 4.13-4.08 (m, 3H), 3.79 (s, 3H), 3.42-3.33 (m, 2H), 3.28-3.20 (m, 2H), 2.95 (dd, J=12.9, 4.8, 1H), 2.72-2.60 (m, 2H), 2.00-1.92 (m, 2H), 1.89-1.79 (m, 3H), 1.65-1.60 (m, 2H), 1.25 (t, J=7.2, 3H). LC/MS (Method A) 7.81 min, [M+1]+ 439.

Aufarbeitung

  1. customThe organic phase was isolated
  2. washfurther washed with an additional portion of a saturated aqueous NaHCO3 solution (1 mL)
  3. dry with materialThe organic component was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to an oil which
  6. customwas purified by silica gel flash chromatography with 10%

Quellen und Nachweise

ORD-Eintrag
ord-4677a87c577045c1aa05da98a6569a2c
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927546B2

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