Methanol → HCID 178501119, compound

HRID 409491Notes

Reaction equation

HRID 409491 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.S(Cl)([Cl:14])=O.[CH3:16]O>>[ClH:14].[CH3:16][O:10][C:9]([C@H:6]1[CH2:5][CH2:4][C@H:3]([CH2:2][NH2:1])[CH2:8][CH2:7]1)=[O:11]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178511262HCID 178511262, compound

Product 1

HCID 178501119HCID 178501119, compoundYield 92%

Procedure

To a solution of trans-4-aminomethyl-1-cyclohexanecarboxylic acid (10 mmol, 1.57 g) in methanol (10 mL) is added of thionyl chloride (12 mmol, 0.88 mL) at 0° C. The mixture is stirred at room temperature for 24 hours and then concentrated under reduced pressure. The residue is washed with hexane to obtain 1.9 g (92%) of trans-4-(aminomethyl)cyclohexanecarboxylic acid methyl ester hydrochloride as white solid. ESI-MS m/z: 172 [M+1]+, Retention time 2.12 min (condition B).

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe residue is washed with hexane

Sources & evidence

ORD record
ord-015d1afde9ca4f19bee8eb05b5d6858d
Source dataset
uspto-grants-2014_06
Patent number
US08759365B2

Reaction notes

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