Tetramethylammonium fluoride → Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylate

HRID 46311

반응식

HRID 46311 반응식
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH:16]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17]1)(C(C)(C)C)(C)C.[F-].C[N+](C)(C)C>O1CCCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([CH:16]2[CH2:17][N:18]([C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[CH2:19]2)[CH:11]=1

참가 물질

4

반응물 2

HCID 67803Tetramethylammonium fluorideHCID 59436503tert-Butyl3-(2-{[tert-butyl(dimethyl)silyl]oxy)-5-chlorophenyl)azetidine-1-carboxylate

생성물 1

HCID 59436608Tert-butyl 3-(5-chloro-2-hydroxyphenyl)azetidine-1-carboxylate수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-Butyl 3-(2-{[tert-butyl(dimethyl)silyl]oxy}-5-chlorophenyl)azetidine-1-carboxylate (Preparation 238, 3.1 g, 7.79 mmol) in tetrahydrofuran (80 ml) was added tetramethylammonium fluoride (1.0 g, 10.74 mmol). The mixture was stirred at room temperature for 18 hours before concentrating in vacuo. The residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution. The organics were dried over sodium sulfate, filtered and evaporated in vacuo to give a reddish brown oil, 2.33 g. This was purified by column chromatography (100 g of silica) eluting with heptane:ethyl acetate (6:4, by volume) to afford the title compound as a reddish brown gum, 850 mg, 38% yield.

후처리

  1. concentrationbefore concentrating in vacuo
  2. customThe residue was partitioned between tert-butyl methyl ether (100 ml) and aqueous sodium hydroxide solution
  3. dry with materialThe organics were dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customto give a reddish brown oil, 2.33 g
  7. customThis was purified by column chromatography (100 g of silica)
  8. washeluting with heptane:ethyl acetate (6:4, by volume)

출처 및 근거

ORD 기록
ord-0a8911d78b43408cb6b6d4cf4c62c707
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541588B2

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