Acetaldehyde → (S)-4-[(benzyl-ethyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

HRID 1911568ノート

反応式

HRID 1911568 の反応式
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24](=O)[CH3:25].[BH3-]C#N.[Na+]>CO.[Cl-].[Cl-].[Zn+2]>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][N:14]([CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:24][CH3:25])[CH2:11][O:10][C:9]1([CH3:23])[CH3:22])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 3

HCID 177AcetaldehydeHCID 5003444Sodium cyanoborohydrideHCID 68714325(S)-4-(benzylamino-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

生成物 1

HCID 68713614(S)-4-[(benzyl-ethyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester収率 18%

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 887Methanol溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of (S)-4-(benzylamino-methyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (800 mg) at r.t. in methanol (10 ml) under an argon atmosphere were added acetaldehyde (0.70 ml), ZnCl2 (1.36 g) and NaBH3CN (0.47 g). The mixture was warmed to 50° C. and stirring at that temperature was continued for 17 h. The mixture was cooled to r.t. and partitioned between ammonium chloride solution and dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/ethyl acetate=1:1) to give (S)-4-[(benzyl-ethyl-amino)-methyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (160 mg, 18%) as colorless oil. MS (ISP): 293.5 ([M-tBu+H]+)

後処理

  1. temperatureThe mixture was cooled to r.t.
  2. custompartitioned between ammonium chloride solution and dichloromethane
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (column: Isolute® Flash-NH2 from Separtis; eluent: heptane/ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-ae753c0259174bb1bd218457ee978110
出典データセット
uspto-grants-2013_12
特許番号
US08604061B2

反応ノート

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