Lithium Hydroxide → (2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenol

HRID 1672543Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1672543
CO[C@H](C1C=CC=CC=1)C([O:6][C@@H:7]1[CH2:16][CH2:15][C:14]2[C:9](=[C:10]([NH2:17])[CH:11]=[CH:12][CH:13]=2)[CH2:8]1)=O.[OH-].[Li+]>O1CCCC1>[NH2:17][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:9]=1[CH2:8][C@H:7]([OH:6])[CH2:16][CH2:15]2

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 91257777HCID 91257777, Verbindung

Produkt 1

HCID 57936087(2R)-8-Amino-1,2,3,4-tetrahydro-2-naphthalenolAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of Example 24D (3.05 g, 9.80 mmol) in tetrahydrofuran (40 mL) and lithium hydroxide (1 M aq, 30 mL, 30.0 mmol) was stirred vigorously at ambient temperature. After 1.5 hours the reaction mixture was partitioned between 100 mL ethyl acetate:H2O (1:1). The separated organic phase was washed with aq saturated NaHCO3 and brine, dried over Na2SO4, and filtered. The solvent was removed at the rotary evaporator to yield 1.31 g (82% yield) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 6.76 (t, 1H), 6.41 (d, 1H), 6.28 (d, 1H), 4.74, (d, 1H), 4.65 (bs, 2H), 3.90 (m, 1H), 2.52-2.79 (m, 3H), 2.16 (m, 1H), 1.83 (m, 1H), 1.55 (m, 1H). MS (DCI+) m/z 164 (M+H)+, 181 (M+NH4)+.

Aufarbeitung

  1. customAfter 1.5 hours the reaction mixture was partitioned between 100 mL ethyl acetate:H2O (1:1)
  2. washThe separated organic phase was washed with aq saturated NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe solvent was removed at the rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-6a75acd2fc6a4656b9829fd1d85c597f
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998993B2

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