Triacetoxyperiodinane → Benzyl 4-formylpiperidine-1-carboxylate

HRID 220830

反応式

HRID 220830 の反応式
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH2:39][OH:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl.C(Cl)(Cl)Cl.O>[CH2:23]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([CH:39]=[O:40])[CH2:35][CH2:34]1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

参加物

6

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 736490Benzyl 4-(hydroxymethyl)piperidine-1-carboxylate

生成物 1

HCID 2776272Benzyl 4-formylpiperidine-1-carboxylate収率 66%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6212Chloroform溶媒HCID 6344Dichloromethane溶媒

実験手順

Dess-Martin reagent (17 g, 39.6 mmol) was added portion-wise to a solution of 4-hydroxymethyl-piperidine-1-carboxylic acid benzyl ester from Example E33.1 (8.33 g, 33 mmol) in dichloromethane (100 ml) at room temperature. The mixture was stirred for 3 h under an inert atmosphere then diluted with chloroform and water and the layers were partitioned. The organic layer was washed with brine, dried and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane) to yield the title compound (5.5 g, 66%).

後処理

  1. customthe layers were partitioned
  2. washThe organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash chromatography on silica gel (eluant; 40% EtOAc:60% hexane)

出典と根拠

ORDレコード
ord-ce0d9e545c534132b12a3dca31da0c12
出典データセット
uspto-grants-2012_06
特許番号
US08202858B2

関連ノート

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