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

HRID 2391021Notes

Reaction equation

HRID 2391021 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-ca7d85ff53d945c9923b0495b073b3bf
Source dataset
uspto-grants-2012_09
Patent number
US08273900B2

Reaction notes

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