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

HRID 891792ノート

反応式

HRID 891792 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1a5fedb0e63b4397837c91184aca0ad6
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

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