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

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).

1. concentrationThe mixture was concentrated to approximately ⅓ of its volume
2. custompartitioned between DCM (200 mL) and water (200 mL)
3. extractionThe aqueous layer was extracted into DCM (3×)
4. washthe combined organic layers were washed with brine
5. dry with materialdried (MgSO4)
6. concentrationconcentrated in vacuo

ORD record

ord-a263df2780b2487f89fffcfa1fd5d381

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315503B2