Sodium Hydroxide → (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol

HRID 75565Notes

Reaction equation

HRID 75565 reaction equation
[OH-].[Na+].FC(F)(F)C([NH:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]([OH:18])[CH2:10][CH2:9]1)=O>CO.O.CO>[NH3:7].[NH2:7][C@@H:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C@H:11]([OH:18])[CH2:10][CH2:9]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 866866722,2,2-Trifluoro-N-((1S,4R)-4-hydroxy-1,2,3,4-tetrahydro-naphthalen-1-yl)-acetamide

Product 2

HCID 222AmmoniaHCID 86686674(1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-olYield 200%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

Sodium hydroxide (2.10 g, 53.0 mmol) was added to an ice cold solution of Intermediate 1c (3.43 g, 13.2 mmol) in MeOH/water (2:1, 50 mL) and stirred for 3.5 h. The mixture was loaded on to a SCX-2 cartridge, eluting with MeOH then 2M NH3 in MeOH, to yield the title compound (2.30 g, 13.2 mmol, 99%). 1H NMR (400 MHz, d6-DMSO): 1.66-1.90 (4H, m), 3.71-3.77 (1H, t, J=5.4 Hz), 4.46-4.54 (1H, t, J=5.4 Hz), 7.14-7.22 (2H, m), 7.32-7.38 (1H, m), 7.40-7.46 (1H, m).

Workup

  1. washeluting with MeOH

Sources & evidence

ORD record
ord-62f464c01a7a4396ba878a23796e6200
Source dataset
uspto-grants-2014_09
Patent number
US08835431B2

Reaction notes

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