Benzaldehyde → 4-Benzylamino-cyclohexanecarboxylic acid tert-butyl ester

HRID 444712Notes

Reaction equation

HRID 444712 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:13][CH2:12][CH:11]([NH2:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Mg+2].[CH:21](=O)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[BH4-].[Na+]>CO.O>[C:1]([O:5][C:6]([CH:8]1[CH2:9][CH2:10][CH:11]([NH:14][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 4311764Sodium borohydrideHCID 18698345tert-Butyl 4-aminocyclohexane-1-carboxylate

Product 1

HCID 687248414-Benzylamino-cyclohexanecarboxylic acid tert-butyl esterYield 100.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 4-amino-cyclohexanecarboxylic acid tert-butyl ester (500 mg, 2.500 mmol) in MeOH (3 mL) is added TEA (140 uL, 1.000 mmol), MgSO4 (452 mg, 3.750 mmol), and benzaldehyde (278 uL, 2.750 mmol). The mixture stirs 1 h. The mixture is then cooled to 0° C. and NaBH4 (568 mg, 15.00 mmol) is added portionwise over 10 min. The mixture stirs 1 h at ambient temperature. Then H2O (20 mL) is added and the mixture is extracted with EtOAc (2×50 mL), dried and concentrated to affords 730 mg of 4-benzylamino-cyclohexanecarboxylic acid tert-butyl ester. LC/MS: [M+H]+ 290, Rt=0.80 min (method 6).

Workup

  1. waitThe mixture stirs 1 h at ambient temperature
  2. extractionthe mixture is extracted with EtOAc (2×50 mL)
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5e9039f2f12d4e88a6cb87c4b568f737
Source dataset
uspto-grants-2013_07
Patent number
US08476224B2

Reaction notes

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