Hydrochloric Acid → Methyl 4-aminocyclohexanecarboxylate

HRID 1944715Notes

Reaction equation

HRID 1944715 reaction equation
CC(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([OH:17])=[O:16])[CH2:11][CH2:10]1)=O)(C)C.[CH3:18]OC(OC)(C)C.Cl.CCOCC>CO>[CH3:18][O:17][C:15]([CH:12]1[CH2:11][CH2:10][CH:9]([NH2:8])[CH2:14][CH2:13]1)=[O:16]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 64952,2-DimethoxypropaneHCID 27559964-(((Tert-butoxy)carbonyl)amino)cyclohexane-1-carboxylic acid

Product 1

HCID 422580Methyl 4-aminocyclohexanecarboxylateYield 103.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(1r,4r)-4-(tert-Butoxycarbonylamino)cyclohexanecarboxylic acid (25 g, 103 mmol) was dissolved in MeOH (250 ml), to which 2,2-dimethoxypropane (10.70 g, 12.63 ml, 103 mmol) and then 2M HCl in ether (51 ml, 103 mmol) were added. The reaction mixture was stirred at room temperature overnight, then concentrated and the residue was treated with ether (100 ml). The resulting white suspension was filtered then dried to afford a white powder (16.8 g, 84% yield).

Workup

  1. concentrationconcentrated
  2. additionthe residue was treated with ether (100 ml)
  3. filtrationThe resulting white suspension was filtered
  4. customthen dried

Sources & evidence

ORD record
ord-d159148976bd42a5a75f9591b7a56504
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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