Methanol → Methyl 1-amino-4-methoxy-4-(methoxymethyl)cyclohexanecarboxylate

HRID 922127Notes

Reaction equation

HRID 922127 reaction equation
S(Cl)(Cl)=O.Cl.[NH2:6][C:7]1([C:18]([OH:20])=[O:19])[CH2:12][CH2:11][C:10]([O:16][CH3:17])([CH2:13][O:14][CH3:15])[CH2:9][CH2:8]1.[CH3:21]O>>[NH2:6][C:7]1([C:18]([O:20][CH3:21])=[O:19])[CH2:12][CH2:11][C:10]([O:16][CH3:17])([CH2:13][O:14][CH3:15])[CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 904137241-Amino-4-methoxy-4-(methoxymethyl)cyclohexanecarboxylic acid hydrochloride

Product 1

HCID 71246293Methyl 1-amino-4-methoxy-4-(methoxymethyl)cyclohexanecarboxylate

Conditions

Temperature
40 °C

Procedure

At 0° C., 4.1 ml (55.60 mmol) of thionyl chloride were added dropwise to 4.70 g of the compound from Example 20A in 50 ml of methanol. The mixture was stirred at 0° C. for 0.5 hours and at 40° C. overnight. After cooling, the mixture was concentrated, the residue was taken up in ethyl acetate and washed with saturated aqueous sodium bicarbonate solution, the aqueous phase was extracted repeatedly with ethyl acetate and the combined organic phases were dried over sodium sulphate, filtered and concentrated. This gave 392 mg (61% of theory from Example 16A) of the title compound as a diastereomer mixture which was reacted without further purification.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. extractionthe aqueous phase was extracted repeatedly with ethyl acetate
  5. dry with materialthe combined organic phases were dried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThis gave 392 mg (61% of theory from Example 16A) of the title compound as a diastereomer mixture which was reacted without further purification

Sources & evidence

ORD record
ord-4476164929a843b09942da0cb7dcba47
Source dataset
uspto-grants-2016_03
Patent number
US09278925B2

Reaction notes

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