Diisopropylethylamine → Methyl 1-({4-[({4-[(trans-2-Hydroxycyclopentyl)oxy]-1,2-benzisoxazol-3-yl}oxy)methyl]piperidin-1-yl}methyl)cyclopentanecarboxylate

HRID 2410366

Reaktionsgleichung

Reaktionsgleichung von HRID 2410366
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][O:8][C:9]2[C:13]3[C:14]([O:18][C@@H:19]4[CH2:23][CH2:22][CH2:21][C@H:20]4[OH:24])=[CH:15][CH:16]=[CH:17][C:12]=3[O:11][N:10]=2)[CH2:3][CH2:2]1.I[CH2:26][C:27]1([C:32]([O:34][CH3:35])=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]1.C(N(CC)C(C)C)(C)C>CN1CCCC1=O.C(OCC)(=O)C.O>[OH:24][C@@H:20]1[CH2:21][CH2:22][CH2:23][C@H:19]1[O:18][C:14]1[C:13]2[C:9]([O:8][CH2:7][CH:4]3[CH2:5][CH2:6][N:1]([CH2:26][C:27]4([C:32]([O:34][CH3:35])=[O:33])[CH2:31][CH2:30][CH2:29][CH2:28]4)[CH2:2][CH2:3]3)=[N:10][O:11][C:12]=2[CH:17]=[CH:16][CH:15]=1

Komponenten

7

Edukt 3

HCID 81531DiisopropylethylamineHCID 67231596Methyl 1-(iodomethyl)cyclopentanecarboxylateHCID 69316225trans-2-{[3-(Piperidin-4-ylmethoxy)-1,2-benzisoxazol-4-yl]oxy}cyclopentanol

Produkt 1

HCID 69318986Methyl 1-({4-[({4-[(trans-2-Hydroxycyclopentyl)oxy]-1,2-benzisoxazol-3-yl}oxy)methyl]piperidin-1-yl}methyl)cyclopentanecarboxylateAusbeute 11 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of trans-2-{[3-(piperidin-4-ylmethoxy)-1,2-benzisoxazol-4-yl]oxy}cyclopentanol (77 mg, 0.23 mmol, EXAMPLE 33, Step 2), methyl 1-(iodomethyl)cyclopentanecarboxylate (75 mg, 0.28 mmol, EXAMPLE 33, Step 1), and N,N-diisopropylethylamine (0.12 mL, 0.70 mmol) in N-methylpyrrolidone (3.0 mL) was heated at 120° C. for 14 h. The mixture was cooled to room temperature and the mixture was diluted with ethyl acetate and water. The mixture was extracted with ethyl acetate (30 mL×2) and washed with brine. The extracts were combined and dried over sodium sulfate and concentrated in vacuo to give a brown solid. The residual solid was purified by silica gel column chromatography (hexane/ethyl acetate 3:2) to give 12 mg (11%) of the title compound as a colorless viscous oil.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate (30 mL×2)
  3. washwashed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customto give a brown solid
  7. customThe residual solid was purified by silica gel column chromatography (hexane/ethyl acetate 3:2)

Quellen und Nachweise

ORD-Eintrag
ord-8b5dfdba53364787aa62430ea025b484
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08816090B2

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