Ethyl Acetate → HCID 59614349、化合物

HRID 409472ノート

反応式

HRID 409472 の反応式
[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C@H:10]([OH:15])[C@@H:9]1[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.CCOC(C)=O>ClCCl.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[C@H:12]([CH2:13][CH3:14])[CH2:11][C:10](=[O:15])[C@@H:9]1[CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 159087TriacetoxyperiodinaneHCID 59614360HCID 59614360、化合物

生成物 1

HCID 59614349HCID 59614349、化合物収率 71.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of (2S,3S,5R)-2-benzyl-5-ethyl-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (0.138 mmol; 42 mg) in dichloromethane (1.4 mL) is added Dess-Martin periodinane (0.166 mmol; 70.4 mg) at 0° C. The mixture is stirred at the same temperature for 1.5 hours. To the mixture, brine and EtOAc are added. The organic layer is separated, washed with saturated aqueous Na2S2O3 solution, dried over Na2SO4, filtered, concentrated under reduced pressure. The residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc) to give (2S,5R)-2-benzyl-5-ethyl-3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester (29.8 mg, 71%); ESI-MS m/z: 248 [M+−tBu+2], Retention time 2.49 min (condition A).

後処理

  1. customThe organic layer is separated
  2. washwashed with saturated aqueous Na2S2O3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is purified by column chromatography on silica gel (eluent; n-hexane/EtOAc)

出典と根拠

ORDレコード
ord-0a595b992eaa40938c532185683ca771
出典データセット
uspto-grants-2014_06
特許番号
US08759365B2

反応ノート

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