Triethylamine → (1R,4S)-4-Amino-1,2,3,4-tetrahydronaphthalen-1-ol
Reaction equation
FC(F)(F)C([O:5][CH2:6][CH3:7])=O.[C@@H:10]1([NH2:20])[C:19]2[C:14](=[CH:15]C=C[CH:18]=2)[CH2:13][CH2:12][CH2:11]1.C(N(CC)CC)C>CO>[NH2:20][C@@H:10]1[C:11]2[C:7](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@H:6]([OH:5])[CH2:18][CH2:19]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Ethyl trifluoroacetate (24.2 mL, 204 mmol) was added dropwise to a solution of (S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)amine (Alfa Aesar; 25.0 g, 170 mmol) and triethylamine (35.5 mL, 255 mmol) in MeOH (250 mL) at RT and stirred for 18 h. The mixture was concentrated to approximately ⅓ of its volume and then partitioned between DCM (200 mL) and water (200 mL). The aqueous layer was extracted into DCM (3×) and the combined organic layers were washed with brine, dried (MgSO4) and concentrated in vacuo to yield the title compound (41.1 g, 169 mmol, 99%). 1H NMR (400 MHz, CDCl3): 1.80-1.95 (3H, m), 2.05-2.15 (1H, m), 2.75-2.90 (2H, m), 5.18-5.25 (1H, q, J 5.0 Hz), 6.38-6.48 (1H, br s), 7.12-7.16 (1H, m), 7.20-7.26 (3H, m).