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Acetic Acid → (1R,2S,3R)-3-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}cyclopentane-1,2-diol

HRID 1401857
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1401857
Cl.[NH2:2][C@@H:3]1[CH2:7][CH2:6][C@@H:5]([OH:8])[C@H:4]1[OH:9].CCN(C(C)C)C(C)C.[CH3:19][C:20]1([CH3:44])[CH2:29][CH2:28][C:27]([CH3:31])([CH3:30])[C:26]2[CH:25]=[C:24]([C:32]3[N:33]=[C:34]([N:37]4[CH2:42][CH2:41][C:40](=O)[CH2:39][CH2:38]4)[S:35][CH:36]=3)[CH:23]=[CH:22][C:21]1=2.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C1COCC1.CN(C=O)C>[CH3:19][C:20]1([CH3:44])[CH2:29][CH2:28][C:27]([CH3:30])([CH3:31])[C:26]2[CH:25]=[C:24]([C:32]3[N:33]=[C:34]([N:37]4[CH2:42][CH2:41][CH:40]([NH:2][C@@H:3]5[CH2:7][CH2:6][C@@H:5]([OH:8])[C@H:4]5[OH:9])[CH2:39][CH2:38]4)[S:35][CH:36]=3)[CH:23]=[CH:22][C:21]1=2
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Komponenten

9

Edukt 6

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 13497975(1R,2S,3R)-3-aminocyclopentane-1,2-diol hydrochlorideHCID 673225751-[4-(5,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-one

Produkt 1

HCID 67325209(1R,2S,3R)-3-{1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-ylamino}cyclopentane-1,2-diol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

24 mg (0.16 mmol) of (1R,2S,3R)-3-aminocyclopentane-1,2-diol hydrochloride are dissolved in 1 ml of THF and 2 ml of DMF, and 27 μl (0.16 mmol) of DIPEA are added. 60 mg (0.16 mmol) of 1-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperidin-4-one are added. The mixture is stirred at room temperature for 30 min, 18 μl (0.32 mmol) of glacial acetic acid are added, and the mixture is stirred for a further 10 min. 70 mg (0.32 mmol) of sodium triacetoxyborohydride are subsequently added. The reaction mixture is stirred at room temperature overnight, a concentrated sodium hydrogencarbonate solution is added, and the mixture is extracted twice with EA. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue is purified by means of preparative HPLC. The product is in the form of the hydrochloride.

Aufarbeitung

  1. stirringthe mixture is stirred for a further 10 min
  2. stirringThe reaction mixture is stirred at room temperature overnight
  3. extractionthe mixture is extracted twice with EA
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue is purified by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-61cc98d5346442cd9b79d5e2369b4404
Quelldatensatz
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08907098B2

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