Tetrabutylammonium Fluoride → 3-Hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

HRID 891809ノート

反応式

HRID 891809 の反応式
[Si]([O:18][CH:19]1[CH2:22][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])[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>[OH:18][CH:19]1[CH2:20][N:21]([C:23]2[O:24][CH:25]=[C:26]([C:28]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[O:29])[N:27]=2)[CH2:22]1

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 222428193-t-Butyldiphenylsilyloxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine

生成物 1

HCID 222429883-Hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine収率 100.6%

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-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (730 mg, 1.48 mmol) (obtained as described in Reference Example 72(1)) in anhydrous tetrahydrofuran (37 ml) was added a solution of 1.0 M tetra-n-butylammonium fluoride in tetrahydrofuran (1.78 ml, 1.78 mmol) in an ice bath and the mixture was stirred in an ice bath for 1.5 hours. After checking the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using ethyl acetate:methanol (95:5→9:1) as the eluant to afford 3-hydroxy-1-(4-morpholinocarbonyl-1,3-oxazol-2-yl)azetidine (377 mg, yield 100%) as white crystals.

後処理

  1. customthe completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-dad8d1a42d67417e9b621675ea235ead
出典データセット
uspto-grants-2006_02
特許番号
US07001897B2

反応ノート

読み込み中…