Methanol → HCID 178501209, compound

HRID 2249967Notes

Reaction equation

HRID 2249967 reaction equation
S(Cl)([Cl:3])=O.[NH2:5][C@@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([OH:14])=[O:13])[CH2:8][CH2:7]1.[CH3:15]O>>[ClH:3].[NH2:5][C@@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]([O:14][CH3:15])=[O:13])[CH2:8][CH2:7]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178511566HCID 178511566, compound

Product 1

HCID 178501209HCID 178501209, compoundYield 81.6%

Procedure

Thionyl chloride (301 mL, 0.6 eq) was added dropwise to a suspension of cis-4-amino-1-cyclohexane carboxylic acid (6) (984 g, 6.87 mol) in methanol (4.82 L) and stirred for 6 hours at room temperature, and the mixture was allowed to be stand for 3 days. The reaction mixture was concentrated under reduced pressure and isopropyl ether was added to the mixture. The appeared crystals were collected by filtration to obtain methyl cis-4-amino-1-cyclohexane carboxylate hydrochloride (1086 g, 81.6%). The mother liquor was concentrated under reduced pressure and methanol (50 mL) and isopropyl ether (1.0 mL) were added to the residue. The appeared crystals were collected by filtration to obtain second crystals of (7) (94 g, 7.0%).

Workup

  1. customfor 3 days
  2. concentrationThe reaction mixture was concentrated under reduced pressure and isopropyl ether
  3. additionwas added to the mixture
  4. filtrationThe appeared crystals were collected by filtration

Sources & evidence

ORD record
ord-451c7f5f29374a0f8c4d3c35d091f9c3
Source dataset
uspto-grants-2008_01
Patent number
US07314950B2

Reaction notes

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