Triacetoxyperiodinane → [(R)-2-(3'-chloro-biphenyl-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl ester

HRID 881874ノート

反応式

HRID 881874 の反応式
[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]([CH2:23][OH:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOC(C)=O>[C:1]([O:5][C:6](=[O:25])[NH:7][C@@H:8]([CH:23]=[O:24])[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=2)=[CH:12][CH:11]=1)([CH3:2])([CH3:4])[CH3:3]

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 67208767HCID 67208767、化合物

生成物 1

HCID 86648198[(R)-2-(3'-chloro-biphenyl-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl ester収率 52.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Next, to a solution of [(R)-2-(3′-chloro-biphenyl-4-yl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester (2.0 g, 5.53 mmol) in DCM (30 mL) is added Dess-Martin periodinane (2.81 g, 6.63 mmol). After being stirred at room temperature for 2 h, the reaction mixture is diluted with EtOAc and washed with saturated NaHCO3 aqueous solution and brine. The organic layer is dried over Na2SO4 and concentrated. The residue is purified by flash column chromatography (silica gel, eluent; heptane/EtOAc=100:0 to 0:100) to give [(R)-2-(3′-chloro-biphenyl-4-yl)-1-formyl-ethyl]-carbamic acid tert-butyl ester (1.05 g). HPLC retention time=1.27 minutes (condition A): MS (m+1)=360.

後処理

  1. washwashed with saturated NaHCO3 aqueous solution and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue is purified by flash column chromatography (silica gel, eluent; heptane/EtOAc=100:0 to 0:100)

出典と根拠

ORDレコード
ord-532abe381c8743df8fec9a99e073252c
出典データセット
uspto-grants-2015_03
特許番号
US08993631B2

反応ノート

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