Acetic Acid → (S)-[2-(3,4-Dichloro-phenyl)-4-(2-oxo-[1,4']bipiperidinyl-1'-yl)-butyl]-methyl-carbamic acid tert-butyl ester

HRID 2221072ノート

反応式

HRID 2221072 の反応式
[N:1]1([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][C:2]1=[O:7].C(O)(=O)C.[C:18]([O:22][C:23](=[O:39])[N:24]([CH2:26][C@H:27]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[CH2:28][CH:29]=O)[CH3:25])([CH3:21])([CH3:20])[CH3:19].[Na]>CO.C(=O)(O)[O-].[Na+]>[C:18]([O:22][C:23](=[O:39])[N:24]([CH2:26][C@H:27]([C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([Cl:38])[CH:32]=1)[CH2:28][CH2:29][N:11]1[CH2:12][CH2:13][CH:8]([N:1]2[CH2:6][CH2:5][CH2:4][CH2:3][C:2]2=[O:7])[CH2:9][CH2:10]1)[CH3:25])([CH3:19])([CH3:20])[CH3:21]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 5360545SodiumHCID 15433413tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamateHCID 21839852[1,4'-Bipiperidin]-2-one

生成物 1

HCID 69224867(S)-[2-(3,4-Dichloro-phenyl)-4-(2-oxo-[1,4']bipiperidinyl-1'-yl)-butyl]-methyl-carbamic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 887Methanol溶媒3 回HCID 516892Sodium Bicarbonate溶媒

実験手順

To a solution of [1,4′]bipiperidinyl-2-one (4.5 g) in methanol (100 mL) was added acetic acid (1.49 mL). The solution was stirred for several minutes before (S)-[2-(3,4-dichloro-phenyl)-4-oxo-butyl]-methyl-carbamic acid tert-butyl ester (26 mmole) was added in methanol (25 mL). Stirring was continued for 20 minutes after which time, sodium cyanoborohyuride (1.64 g) was then added in methanol (5 mL). The mixture was stirred for two days and then diluted with aqueous sodium bicarbonate and concentrated. It was then partitioned between layers of water and dichloromethane. The aqueous layers were washed with dichloromethane and the organic phases were combined, dried and evacuated to viscous oil which was purified by flash chromatography eluting with methanol:dichloromethane (5:95). This material formed a white foam upon drying under vacuum (9.4 g). MS: m/z=512(M+1).

後処理

  1. stirringThe mixture was stirred for two days
  2. concentrationconcentrated
  3. customIt was then partitioned between layers of water and dichloromethane
  4. washThe aqueous layers were washed with dichloromethane
  5. customdried
  6. customevacuated to viscous oil which
  7. customwas purified by flash chromatography
  8. washeluting with methanol:dichloromethane (5:95)
  9. customThis material formed a white foam
  10. customupon drying under vacuum (9.4 g)

出典と根拠

ORDレコード
ord-fcbc2040e6eb416ba25b07fcf3798d9a
出典データセット
uspto-grants-2008_05
特許番号
US07368461B2

反応ノート

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