Hydrochloric Acid → (S)-6,6-dimethylmorpholine-3-carboxylic acid hydrochloride

HRID 524584Notes

Reaction equation

HRID 524584 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][NH:6][C@H:5]([C:8]([O:10]C)=[O:9])[CH2:4][O:3]1.[OH-].[Na+].[ClH:15]>CO.O>[ClH:15].[CH3:1][C:2]1([CH3:12])[CH2:7][NH:6][C@H:5]([C:8]([OH:10])=[O:9])[CH2:4][O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53338736(S)-Methyl 6,6-dimethyl-morpholine-3-carboxylate

Product 1

HCID 53487570(S)-6,6-dimethylmorpholine-3-carboxylic acid hydrochlorideYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of (S)-methyl 6,6-dimethylmorpholine-3-carboxylate (0.2 g, 1.2 mmol) (The compound was synthesized according to the procedure as described in WO2008024692) in anhydrous methanol (4 mL) was added a solution of sodium hydroxide (0.1 g, 2.4 mmol) in water (1 mL). The reaction mixture was stirred at 25° C. for 2 hours, and cooled to 0° C. The reaction mixture was adjusted to pH 1-2 with con. HCl. The mixture was concentrated in vacuo to give the title compound as a white solid (0.19 g, 100%). The compound was characterized by the following spectroscopic data:

Workup

  1. temperaturecooled to 0° C
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-882165da59c647078e979c59fc100e57
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

Loading…