Hydrochloric Acid → 1-Aminomethyl-5,6-bis(trimethylacetoxy)-3,4-dihydro-3-phenyl-naphthalene hydrochloride

HRID 233391Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 233391
C(OC([NH:8][CH2:9][C:10]1[C:19]2[C:14](=[C:15]([O:27][C:28](=[O:33])[C:29]([CH3:32])([CH3:31])[CH3:30])[C:16]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:18]=2)[CH2:13][CH:12]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH:11]=1)=O)(C)(C)C.[ClH:40]>O1CCOCC1>[ClH:40].[NH2:8][CH2:9][C:10]1[C:19]2[C:14](=[C:15]([O:27][C:28](=[O:33])[C:29]([CH3:30])([CH3:31])[CH3:32])[C:16]([O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:17][CH:18]=2)[CH2:13][CH:12]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH:11]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 19961074N-t-Butyloxycarbonyl-1-aminomethyl-5,6-bis(trimethylacetoxy)-3,4-dihydro-3-phenyl naphthalene

Produkt 1

HCID 199612231-Aminomethyl-5,6-bis(trimethylacetoxy)-3,4-dihydro-3-phenyl-naphthalene hydrochlorideAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

N-t-Butyloxycarbonyl-1-aminomethyl-5,6-bis(trimethylacetoxy)-3-phenyl-3,4-dihydronaphthalene (14 g, 26 mmol), from Step 2, was dissolved in 75 mL of dioxane and saturated with anhydrous hydrogen chloride. The reaction mixture was stirred for 2 h and concentrated in vacuo. The solid residue was dissolved in a minimum amount of methanol and the methanol solution was added dropwise to an excess amount (500 mL) of diethyl ether. The precipitate was filtered, washed with diethyl ether and dried to give 9.1 g (90% yield) of 1-aminomethyl-5,6-bis(trimethylacetoxy)-3-phenyl-3,4-dihydronaphthalene hydrochloride as a white powder, m.p. 210°-212° C.; 1H NMR (d6 -DMSO) δ: 1.25 (s, 9H), 1.28 (s, 9H), 2.61 (dd, 1H), 2.89 (dd, 1H), 3.75-3.85 (m, 1H), 3.99 (s, 2H), 6.28 (d, 2H), 7.15 (d, 1H), 7.2-7.35 (m, 5H), 7.37 (d, 1H), 8.37 (br s, 3H).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. dissolutionThe solid residue was dissolved in a minimum amount of methanol
  3. additionthe methanol solution was added dropwise to an excess amount (500 mL) of diethyl ether
  4. filtrationThe precipitate was filtered
  5. washwashed with diethyl ether
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d0c904c754494d7fa95c7e82326f976e
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05591884

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