Hydrochloric Acid → 2,2,2-Trichloroethyl 2-[4-chloro-2-(hydroxymethyl)phenyl]azetidine-1-carboxylate

HRID 1058260노트

반응식

HRID 1058260 반응식
[OH-].[Na+].Cl.[NH:4]1[CH2:7][CH2:6][CH:5]1[C:8]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=1[CH2:15][OH:16].[Cl:17][C:18]([Cl:25])([Cl:24])[CH2:19][O:20][C:21](Cl)=[O:22].Cl>O1CCOCC1.O>[Cl:14][C:11]1[CH:12]=[CH:13][C:8]([CH:5]2[CH2:6][CH2:7][N:4]2[C:21]([O:20][CH2:19][C:18]([Cl:25])([Cl:24])[Cl:17])=[O:22])=[C:9]([CH2:15][OH:16])[CH:10]=1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 870632,2,2-Trichloroethyl chloroformateHCID 69939797(2-Azetidin-2-yl-5-chlorophenyl)methanol hydrochloride

생성물 1

HCID 186724042,2,2-Trichloroethyl 2-[4-chloro-2-(hydroxymethyl)phenyl]azetidine-1-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

Aqueous sodium hydroxide (1 M, 2.67 mL) was added to a stirred solution of (2-azetidin-2-yl-5-chlorophenyl)methanol hydrochloride (0.312 g, 1.33 mmol) and trichloroethoxycarbonyl chloride (0.184 mL, 1.33 mmol) in dioxane (8 mL) and water (0.4 mL) at 0° C. The reaction was warmed to ambient temperature and after 1 h was acidified with 1 M HCl solution, extracted into ether, dried (Na2SO4) and evaporated in vacuo to an oil. The crude product was purified by flash column chromatography on silica (eluting with 5% methylene chloride/10-50% ethyl acetate/hexanes gradient) to give 2,2,2-trichloroethyl 2-[4-chloro-2-(hydroxymethyl)phenyl]azetidine-1-carboxylate (283 mg a colorless gum: 1H NMR (CDCl3, 400 MHz) δ 2.24 (br m, 1H), 2.78 (m, 1H), 4.20 (br s, 2H), 4.61 (br m, 2H), 4.68 (br m, 2H), 5.66 (dd, J=8.6, 6.4 Hz, 1H), 7.34 (m, 2H), 7.56 (d, J=8.1 Hz, 1H).

후처리

  1. extractionextracted into ether
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo to an oil
  4. customThe crude product was purified by flash column chromatography on silica (eluting with 5% methylene chloride/10-50% ethyl acetate/hexanes gradient)

출처 및 근거

ORD 기록
ord-f00c8f781fca4bcd8a91aad770406694
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06515011B2

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