Trifluoroacetic acid → N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine

3-{[(2,4-dichlorobenzyl)-(3-hydroxy-3-methyl-butyl)-amino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester (88 mg, 0.2 mmol) is added to a stirred solution of dichloromethane (1.0 mL) and anisole (1.5 mL). Trifluoroacetic acid (0.6 mL) is added and the reaction is stirred for 2 h at room temperature. The reaction is concentrated to half volume and loaded onto a SCX-2 (10 g) column and washed with methanol (40 mL). The product is then eluted with 2M ammonia in methanol (25 mL) and concentrated to yield (57 mg, 87%) of N-(3-hydroxy-3-methylbutyl)-N-{[2,4-dichlorophenyl]-methyl}-azetidine-3-yl-methylamine. 1H NMR (400 MHz, CD3OD) δH: 7.49-7.47 (2H, m), 7.36-7.33 (1H, m), 3.80-3.70 (2H, m), 3.65 (2H, s), 3.49-3.40 (2H, m), 3.16-3.06 (1H, m), 2.79-2.77 (2H, m), 2.67 (2H, t, J=7.3 Hz), 1.69 (2H, t, J=7.3 Hz), 1.1 (6H, s). Mass spectrum (ion spray): m/z=331.2 (M+H).

1. concentrationThe reaction is concentrated to half volume
2. washwashed with methanol (40 mL)
3. washThe product is then eluted with 2M ammonia in methanol (25 mL)
4. concentrationconcentrated

ORD 기록

ord-8511230dbb68459b98958679eb472281

출처 데이터셋

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07615648B2