Ethanol → tert-butyl N-((4-(aminomethyl)cyclohexyl)methyl)carbamate

HRID 1986865Notes

Reaction equation

HRID 1986865 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH2:15][NH:16]C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].CCO.Cl.O1CCOCC1>C(Cl)(Cl)Cl>[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH:9]1[CH2:10][CH2:11][CH:12]([CH2:15][NH2:16])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 204431481,4-Dioxane hydrochlorideHCID 22668023[4-(Tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester

Product 1

HCID 2756046tert-butyl N-((4-(aminomethyl)cyclohexyl)methyl)carbamateYield 47%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of [4-(tert-butoxycarbonylamino-methyl)-cyclohexylmethyl]-carbamic acid tert-butyl ester (11.00 g, 32 mmol) dissolved in 2:1 CHCl3:EtOH at room temperature was added 4.0 M HCl/dioxane (16.1 mL). The mixture was stirred at room temperature for 4 h then concentrated in vacuo to provide a crude white solid. The crude material was purified by silica gel chromatography using a gradient elution of 10-50% (2% NH4OH, 18% MeOH, 80% CH2Cl2)/CH2Cl2. The product-containing fractions were combined and concentrated in vacuo to provide (4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester as a white powder 3.62 g, 47%, m/z calculated for C13H26N2O2: 242.4, found: 243.3 (M+H)+.

Workup

  1. concentrationthen concentrated in vacuo
  2. customto provide a crude white solid
  3. customThe crude material was purified by silica gel chromatography
  4. washa gradient elution of 10-50% (2% NH4OH, 18% MeOH, 80% CH2Cl2)/CH2Cl2
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fec74920f05143459c2a0a861940e640
Source dataset
uspto-grants-2009_06
Patent number
US07550473B2

Reaction notes

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