Diisopropylethylamine → HCID 58171517, Verbindung

To a stirred, ice-cold solution of methyl 4-phenylpiperidine-4-carboxylate hydrochloride (983 mg, 3.8 mmol) and i-Pr2NEt (1.88 mL, 10.5 mmol) in CH2Cl2 (25 mL) was added 2-adamantyl chloroformate (750 mg, 3.5 mmol). The ice bath was allowed to melt and the mixture was stirred overnight at rt. The mixture was diluted with ether (150 mL), washed with 5% aq HCl (2×30 mL) and satd aq NaHCO3 (30 mL) and dried over MgSO4. Removal of the solvent left the crude product (1.37 g, 99%) as a white solid. A 40-mg portion was purified by prep HPLC to afford the title compound (32 mg). LC-MS Method 1 tR=2.4 min, m/z=398, 1H NMR (CDCl3) 1.58 (m, 2H), 1.70-2.10 (14H), 2.56 (d, 2H), 3.10 (br d, 2H), 3.68 (s, 3H), 4.08 (d, 2H), 4.83 (s, 1H), 7.27 (m, 1H), 7.36 (m, 4H).

1. washwashed with 5% aq HCl (2×30 mL)
2. dry with materialdried over MgSO4
3. customRemoval of the solvent
4. waitleft the crude product (1.37 g, 99%) as a white solid
5. customA 40-mg portion was purified by prep HPLC

ORD-Eintrag

ord-10f5305a8a5941a69c6adb635daaed01

Quelldatensatz

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09163012B2