p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

A solution of the product of Example 82C (9 mg, 0.027 mmol) in methanol (10 mL) was treated with PtO2 (10 mg). The reaction flask was evacuated and purged with nitrogen (4 cycles), then with hydrogen (5 cycles), and the suspension was stirred at room temperature under hydrogen (1 atm) for 40 hours. The flask was evacuated and purged with nitrogen (5 cycles) and the mixture was filtered through a pad of diatomaceous earth with methanol (5 mL) rinse. The filtrate was concentrated under vacuum and the residue was taken up in ethyl acetate (1 mL). A solution of p-toluenesulfonic acid monohydrate (5.5 mg, 0.029 mmol) in ethyl acetate (0.5 mL) was added, and the mixture was stirred for 30 minutes, then concentrated under vacuum. The residual solid was triturated with ethyl acetate (0.2 mL) and dried under vacuum to provide the title compound as the p-toluenesulfonate salt: 1H NMR (300 MHz, methanol-d4) δ ppm 1.72-1.87 (m, 2H), 1.97-2.09 (m, 2H), 2.14 (s, 2H), 2.15 (s, 1H), 2.19-2.31 (m, 1H), 2.35 (s, 3H), 2.41-2.71 (m, 2H), 2.81 (s, 1H), 2.96 (s, 2H), 2.99-3.15 (m, 3H), 3.37-3.53 (m, 2H), 3.57-3.69 (m, 1H), 4.15-4.29 (m, 2H), 4.29-4.38 (m, J=4.8 Hz, 1H), 5.02-5.13 (m, 1H), 7.08-7.26 (m, 4H), 7.45 (t, J=7.7 Hz, 1H), 7.53 (d, J=7.9 Hz, 1H), 7.64 (d, J=8.3 Hz, 2H); MS (DCI) m/z 337 (M+H)+.

1. customThe reaction flask was evacuated
2. custompurged with nitrogen (4 cycles)
3. customThe flask was evacuated
4. custompurged with nitrogen (5 cycles)
5. filtrationthe mixture was filtered through a pad of diatomaceous earth with methanol (5 mL)
6. washrinse
7. concentrationThe filtrate was concentrated under vacuum
8. stirringthe mixture was stirred for 30 minutes
9. concentrationconcentrated under vacuum
10. customThe residual solid was triturated with ethyl acetate (0.2 mL)
11. customdried under vacuum

ORD record

ord-b1a6d7d04c9846ef920636e23416da13

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09063126B2