Diethyl Ether → HCID 18457668、化合物

HRID 1272516ノート

反応式

HRID 1272516 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[CH:16]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[CH:23]=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:25][Mg]Br.CCOCC.[Cl-].[NH4+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]2[CH:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:15][CH2:14][CH2:13][CH:12]2[CH:23]([OH:24])[CH3:25])(=[O:9])=[O:10])=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 184576701-(4-Chloro-benzenesulfonyl)-6-phenyl-piperidine-2-carbaldehydeHCID 178418573HCID 178418573、化合物

生成物 1

HCID 18457668HCID 18457668、化合物収率 100%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of the product of step 1 (232 mg; 0.64 mmol) in THF (6 mL) at 0° C. was added methyl magnesium bromide solution 3 N in Et2O (0.27 mL; 0.83 mmol) and the reaction was allowed to warm to room temperature for 1 h. The mixture was poured into saturated ammonium chloride, extracted with DCM, and dried over Na2SO4. After concentration of the solvents, the residue was purified by chromatography over silica gel (eluting Hexanes/EtOAc 8:2) to give 240 mg (100%) of 1-[1-(4-chloro-benzenesulfonyl)-6-phenyl-piperidin-2-yl]-ethanol as a ca 4.5:1 mixture of diastereoisomers.

後処理

  1. extractionextracted with DCM
  2. dry with materialdried over Na2SO4
  3. customAfter concentration of the solvents, the residue was purified by chromatography over silica gel (eluting Hexanes/EtOAc 8:2)

出典と根拠

ORDレコード
ord-f648c4e641764845a0c767906493557d
出典データセット
uspto-grants-2007_04
特許番号
US07208602B2

反応ノート

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