Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid methyl ester

HRID 2361583

Reaction equation

HRID 2361583 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

HCID 216279964-Benzylamino-cyclohexanecarboxylic acid methyl esterYield 47%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8ba29f82b691470d82f549acfb926b9e
Source dataset
uspto-grants-2014_04
Patent number
US08691756B2

Linked notes

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