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

HRID 1672543Notes

Reaction equation

HRID 1672543 reaction equation
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

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 91257777HCID 91257777, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-6a75acd2fc6a4656b9829fd1d85c597f
Source dataset
uspto-grants-2011_08
Patent number
US07998993B2

Reaction notes

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