Tetrabutylammonium Fluoride → 1-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine

HRID 891792노트

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HRID 891792 반응식
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[S:24][CH:25]=[C:26]([CH2:28][N:29]3[C:33](=[O:34])[C:32]4=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]4[C:30]3=[O:39])[N:27]=2)[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[C:30]1(=[O:39])[N:29]([CH2:28][C:26]2[N:27]=[C:23]([N:21]3[CH2:20][CH:19]([OH:18])[CH2:22]3)[S:24][CH:25]=2)[C:33](=[O:34])[C:32]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:31]12

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 222427393-t-Butyldiphenylsilyloxy-1-(4-phthalimidomethyl-1,3-thiazol-2-yl)azetidine

생성물 1

HCID 222428071-(4-Phthalimidomethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine수율 106.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 3-t-butyldiphenylsilyloxy-1-(4-phthalimidomethyl-1,3-thiazol-2-yl)azetidine (1.52 g, 2.57 mmol) (obtained as described in Reference Example 68(1)) in anhydrous tetrahydrofuran (76 ml) was added a 1.0 M solution of tetra-n-butylammonium fluoride in tetrahydrofuran (3.29 ml, 3.29 mmol) in an ice bath and the mixture was stirred in an ice bath for 1 hour. After checking the completion of the reaction, the mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate as the eluant to afford 1-(4-phthalimidomethyl-1,3-thiazol-2-yl)-3-hydroxyazetidine (864 mg, yield 100%) as a white solid.

후처리

  1. customthe completion of the reaction
  2. customthe mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
  3. washThe organic layer was washed with saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on a silica gel column

출처 및 근거

ORD 기록
ord-1a5fedb0e63b4397837c91184aca0ad6
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001897B2

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