Trifluoroacetic acid → HCID 19925593, compound

HRID 1647507Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[C:11]([C:15]2([OH:21])[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:12]=[CH:13][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice-cooled solution of 4-(3-t-butyloxycarbonylaminophenyl)-4-hydroxytetrahydropyran (2.0 g, 6.8 mmol), prepared as in step 2, in dichloromethane (14 mL) was added trifluoroacetic acid (14, mL). The resulting solution was stirred for 0.25 hours at 0° C. and 1 hour at ambient temperature. The volatiles were removed in vacuo and the resulting solution was basified with saturated aqueous potassium carbonate. The resulting mixture was diluted with dichloromethane and the layers separated. The aqueous layer was extracted (4×, dichloromethane). The combined organic layers were dried (MgSO4), and concentrated in vacuo to provide a solid. Trituration with hexanes provided 4-(3-aminophenyl)-4-hydroxytetrahydropyran as a colorless solid (1.01 g, 77%). mp 154°-155° C. 1H NMR (300 MHz, CDCl3) δ7.17 (1H, dt, J=7.5, 1 Hz), 6.84-6.88 (2H, m), 6.62 (1H, br d, J=7.5 Hz), 3.93 (2H, td, J=12, 12, 2.5 Hz), 3.84 (2H, ddd, J=12, 5, 1.5 Hz), 2.05-32 (4H, m). MS m/e 193 (M+NH4 --H2O)+, 211 (M+NH4)+.

Workup

customThe volatiles were removed in vacuo
additionThe resulting mixture was diluted with dichloromethane
customthe layers separated
extractionThe aqueous layer was extracted (4×, dichloromethane)
dry with materialThe combined organic layers were dried (MgSO4)
concentrationconcentrated in vacuo
customto provide a solid

Sources & evidence

ORD record: ord-aca13c46b86c4fa0ab69e3d54f7ff314
Source dataset: uspto-grants-1995_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05432194

Reaction notes

Loading…