Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid methyl ester

HRID 2361583

反応式

HRID 2361583 の反応式
Cl.[CH3:2][O:3][C:4]([C@H:6]1[CH2:11][CH2:10][C@H:9]([NH2:12])[CH2:8][CH2:7]1)=[O:5].[O-]S([O-])(=O)=O.[Mg+2].[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[BH4-].[Na+]>CO.O>[CH3:2][O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:12][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:7]1)=[O:5]

参加物

7

反応物 4

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 178501210HCID 178501210、化合物

生成物 1

HCID 216279964-Benzylamino-cyclohexanecarboxylic acid methyl ester収率 47%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

To a solution of trans-4-amino-cyclohexylcarboxylic acid methyl ester hydrochloride (4.5 g, 23.24 mmol) in MeOH (30 mL) is added TEA (1.3 mL, 9.339 mmol), MgSO4 (4.2 g, 34.88 mmol), and benzaldehyde (2.5 mL, 24.74 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (5.0 g, 132.2 mmol) is added portionwise over 0.5 h. The mixture stirs 1 h at ambient temperature. Then H2O (200 mL) is added and the mixture is extracted with EtOAc (2×500 mL), dried and concentrated. The resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which affords 2.7 g of 4-benzylamino-cyclohexanecarboxylic acid methyl ester. LC/MS: [M+H]+ 248, Rt=0.82 min (method 11).

後処理

  1. waitThe mixture stirs 1 h at ambient temperature
  2. extractionthe mixture is extracted with EtOAc (2×500 mL)
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting solid is purified by flash chromatography (gradient elution: 0-100% EtOAc/Hep) which

出典と根拠

ORDレコード
ord-8ba29f82b691470d82f549acfb926b9e
出典データセット
uspto-grants-2014_04
特許番号
US08691756B2

関連ノート

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