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ChemicalBook CAS DataBase List (R)-1-(2,6-Dichloro-3-fluorophenyl)ethanol
288385-87-5

(R)-1-(2,6-Dichloro-3-fluorophenyl)ethanol synthesis

3synthesis methods
7-(N-tert-Butoxycarbonylpiperidin-4-ylmethoxy)-6-methoxy-3-pivaloyloxymethyl-3,4-dihydroquinazolin-4-one

264208-86-8
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(R)-1-(2,6-Dichloro-3-fluorophenyl)ethanol

288385-87-5
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Yield:288385-87-5 92%

Reaction Conditions:

Stage #1: 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroxyquinazolin-4-onewith trifluoroacetic acid in dichloromethane at 18 - 25; for 1 h;
Stage #2: with sodium hydrogencarbonate in water;ethyl acetate;

Steps:

2c Example 2c

A solution of 7-(1-(tert-butoxycarbonyl)piperidin-4-ylmethoxy)-6-methoxy-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (2.32g, 4.6mmol) in methylene chloride (23ml) containing TFA (5ml) was stirred at ambient temperature for 1 hour. The volatiles were removed under vacuum. The residue was partitioned between ethyl acetate and sodium hydrogen carbonate. The organic solvent was removed under vacuum and the residue was filtered. The precipitate was washed with water, and dried under vacuum. The solid was azeotroped with toluene and dried under vacuum to give 6-methoxy-7-(piperidin-4-ylmethoxy)-3-((pivaloyloxy)methyl)-3,4-dihydroquinazolin-4-one (1.7g, 92%). MS - ESI: 404 [MH]+ 1H NMR Spectrum: (DMSOd6; CF3COOD) 1.15 (s, 9H), 1.45-1.6 (m, 2H), 1.95 (d, 2H), 2.1-2.25 (m, 1H), 2.95 (t, 2H), 3.35 (d, 2H), 3.95 (s, 3H), 4.1 (d, 2H), 5.95 (s, 2H), 7.23 (s, 1H), 7.54 (s, 1H), 8.45 (s, 1H)

References:

EP1244647,2006,B1 Location in patent:Page/Page column 23

123855-51-6 Synthesis
N-Boc-4-piperidinemethanol

123855-51-6
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(R)-1-(2,6-Dichloro-3-fluorophenyl)ethanol

288385-87-5
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193002-25-4 Synthesis
7-Hydroxy-6-methoxy-3-[(pivaloyloxy)methyl]-3,4-dihydroquinazolin-4-one

193002-25-4
4 suppliers
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(R)-1-(2,6-Dichloro-3-fluorophenyl)ethanol

288385-87-5
3 suppliers
inquiry