Sodium Bicarbonate → HCID 178501207, compound

HRID 1257695Notes

Reaction equation

HRID 1257695 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][CH2:3]1.[C:11](=O)(O)[O-].[Na+]>CO.S(=O)(=O)(O)O>[CH3:11][O:9][C:8]([C@H:5]1[CH2:6][CH2:7][C@H:2]([NH2:1])[CH2:3][CH2:4]1)=[O:10]

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 178511567HCID 178511567, compound

Product 1

HCID 178501207HCID 178501207, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of trans 4-amino-cyclohexanecarboxylic acid (12.5 g, 87.0 mmol) in methanol (400 mL) and conc. sulphuric acid (9.0 mL) was stirred at room temperature for one week. The mixture was then neutralised with sodium bicarbonate and the solvent was concentrated under vacuum. The residue was taken into water and continuously extracted with DCM for 18 hours. The organic phase was dried over sodium sulphate and concentrated under vacuum to afford 9.20 g (67%) of trans 4-amino-cyclohexanecarboxylic acid methyl ester as an oil. 1H NMR (400 MHz, CDCl3): δ 3.67 (s, 3H), 2.67 (tt, 1H), 2.24 (tt, 1H), 2.02-1.90 (m, 4H), 1.55-1.41 (m, 2H), 1.19-1.10 (m, 2H).

Workup

  1. concentrationthe solvent was concentrated under vacuum
  2. extractioncontinuously extracted with DCM for 18 hours
  3. dry with materialThe organic phase was dried over sodium sulphate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1cb642b2988848e9a4b3c158a2c6c1b3
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

Loading…