Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid methyl ester

HRID 2361583

반응식

HRID 2361583 반응식
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]

참가 물질

7

반응물 4

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 178501210HCID 178501210, 화합물

생성물 1

HCID 216279964-Benzylamino-cyclohexanecarboxylic acid methyl ester수율 47%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8ba29f82b691470d82f549acfb926b9e
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08691756B2

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