Water → 1-[(Tert-butoxycarbonyl)oxy]piperidin-4-yl methanesulfonate

HRID 2282245ノート

反応式

HRID 2282245 の反応式
[C:1]([O:5][C:6]([O:8][N:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18].CCOC(C)=O.O>C1COCC1>[CH3:16][S:17]([O:15][CH:12]1[CH2:13][CH2:14][N:9]([O:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:10][CH2:11]1)(=[O:19])=[O:18]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 224464201-(Tert-butoxycarbonyloxy)piperidin-4-ol

生成物 1

HCID 866496051-[(Tert-butoxycarbonyl)oxy]piperidin-4-yl methanesulfonate収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 1-[(tert-butoxycarbonyl)oxy]piperidin-4-ol (10.0 g, 49.7 mmol) in THF (200 mL), were added TEA (20.7 mL, 149 mmol) and methanesulfonyl chloride (7.69 mL, 99.4 mmol) at 0° C. The mixture was stirred for 2.5 h at the same temperature. To the mixture was added EtOAc (100 mL) and water (100 mL) and then organic layer has been separated. The aqueous layer has been extracted with EtOAc (50 mL) and the combined organic layer was washed with brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate and then insoluble materials were removed by filtration. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→50/50). Concentration of appropriate fractions afforded crude product, which was washed with a 1:1 mixture of diethyl ether and hexane (50 mL) to give title compound (12.9 g, 92%) as a pale yellow solid.

後処理

  1. customorganic layer has been separated
  2. extractionThe aqueous layer has been extracted with EtOAc (50 mL)
  3. washthe combined organic layer was washed with brine (30 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. custominsoluble materials were removed by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (EtOAc/hexane=20/80→50/50)
  8. customConcentration of appropriate fractions afforded crude product, which
  9. washwas washed with a 1:1 mixture of diethyl ether and hexane (50 mL)

出典と根拠

ORDレコード
ord-7ead01e339574d639695116a52a07b5c
出典データセット
uspto-grants-2015_09
特許番号
US09139589B2

反応ノート

読み込み中…