Methanol → methyl (1R,2S)-2-aminocyclohexanecarboxylate

HRID 7021Notes

Reaction equation

HRID 7021 reaction equation
S(Cl)(Cl)=O.[NH2:5][C@H:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C@H:7]1[C:12]([OH:14])=[O:13].[CH3:15]O>>[CH3:15][O:13][C:12]([C@@H:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C@@H:6]1[NH2:5])=[O:14]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 2724639(1R,2S)-2-Aminocyclohexane-1-carboxylic acid

Product 1

HCID 24751169methyl (1R,2S)-2-aminocyclohexanecarboxylate

Procedure

Thionyl chloride (5.48 g, 46.1 mmol) was added dropwise to a solution of cis-2-aminocyclohexanecarboxylic acid (2.0 g, 14.0 mmol) in methanol (50 mL) at 0° C. The mixture was allowed to warm to room temperature and stir for 18 h. The clear solution was then evaporated to dryness, and the residual volatiles were removed on high vacuum. The crude product, cis-2-aminocyclohexanecarboxylic acid methyl ester, was isolated in quantitative yield and used in the next reaction without purification: 1H NMR (400 MHz, CDCl3) δ 8.50 (s br, 2 H), 3.78 (s, 3 H), 3.59 (s br, 1 H), 3.18 (s br, 1 H), 2.27 (m, 1 H), 2.08 (m, 1 H), 1.88 (m, 2 H), 1.45 (m, 4 H).

Workup

  1. customThe clear solution was then evaporated to dryness
  2. customthe residual volatiles were removed on high vacuum

Sources & evidence

ORD record
ord-bcf6bf420bc14bbda24033646b1b1b0a
Source dataset
uspto-grants-2006_08
Patent number
US07084178B2

Reaction notes

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