Acetic Acid → 1,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylate

HRID 419405ノート

反応式

HRID 419405 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][C:15](=O)[CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10].[C:19]([N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CC(O)=O>ClCCCl.C(Cl)Cl.C([O-])(O)=O.[Na+]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]2[CH2:17][CH2:16][CH:15]([N:29]3[CH2:28][CH2:27][N:26]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:31][CH2:30]3)[CH2:14][CH:13]=2)[CH:6]=[CH:7][C:8]=1[N+:9]([O-:11])=[O:10]

参加物

8

反応物 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 594528844-[3-(Methyloxy)-4-nitrophenyl]-3-cyclohexen-1-one

生成物 1

HCID 594529421,1-Dimethylethyl 4-{4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-yl}-1-piperazinecarboxylate収率 77%

試薬・触媒・溶媒 3

HCID 111,2-Dichloroethane溶媒HCID 6344Dichloromethane溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

A solution of 4-[3-(methyloxy)-4-nitrophenyl]-3-cyclohexen-1-one (514 mg, 2.08 mmol) and 1-BOC-piperazine (430 mg, 2.28 mmol) were stirred in DCE (8 mL) at rt under N2. To this mixture was added sodium triacetoxyborohydride (610 mg, 2.89 mmol) and HOAc (125 mg, 2.08 mmol). The reaction was stirred for approximately 24 h. The reaction was diluted with DCM and aqueous (saturated) NaHCO3. The aqueous layer was extracted with DCM (3×). The combined organic layers were dried over MgSO4, filtered, then concentrated and purified by silica gel chromatography to give the title compound of step E (669 mg, 1.60 mmol, 77%) as a tan solid. MS (ESI): 418 [M+H]+.

後処理

  1. extractionThe aqueous layer was extracted with DCM (3×)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. custompurified by silica gel chromatography

出典と根拠

ORDレコード
ord-c0d6cf88363540c7bfbe172361d8cbef
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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