Benzylamine → 4-Benzylamino-3-methyl-cyclohexanecarboxylic acid ethyl ester

HRID 1914659Notes

Reaction equation

HRID 1914659 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][C:9](=O)[CH:8]([CH3:13])[CH2:7]1)=[O:5])[CH3:2].[CH2:14]([NH2:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][CH:9]([NH:21][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:8]([CH3:13])[CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 57465910Ethyl 3-methyl-4-oxocyclohexane-1-carboxylate

Product 1

HCID 574659114-Benzylamino-3-methyl-cyclohexanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture comprising 3-methyl-4-oxo-cyclohexanecarboxylic acid ethyl ester (1.00 g, 5.43 mmol) and benzylamine (0.58 g, 5.43 mmol) in DCE (50 mL) is treated with sodium triacetoxyborohydride (2.30 g, 10.9 mmol) and stirred at RT for 2 hours. The mixture is partitioned between DCM and water and the organic portion is separated, dried (MgSO4) and concentrated in vacuo. Purification by chromatography on silica eluting with iso-hexane:EtOAc (4:1 increasing to 1:1) affords the title compound. 1H NMR (400 MHz, DMSO-d6) δ 7.32 (4H, m), 7.20 (1H, m) 4.04 (2H, q), 3.72 (2H, m), 2.50-1.30 (9H, m), 1.19 (4H, m), 0.89 (3H, d).

Workup

  1. customThe mixture is partitioned between DCM and water
  2. customthe organic portion is separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customPurification by chromatography on silica eluting with iso-hexane:EtOAc (4:1 increasing to 1:1)

Sources & evidence

ORD record
ord-f7ddfc3332134894873db77e428cb1fb
Source dataset
uspto-grants-2013_12
Patent number
US08614213B2

Reaction notes

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