Acetic Anhydride → cis-Methyl 3-acetamidocyclohexanecarboxylate

HRID 2176931Notes

Reaction equation

HRID 2176931 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]1>N1C=CC=CC=1>[C:1]([NH:8][C@@H:9]1[CH2:14][CH2:13][CH2:12][C@H:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 68466059Methyl (1S,3R)-3-aminocyclohexane-1-carboxylate

Product 1

HCID 131730829cis-Methyl 3-acetamidocyclohexanecarboxylateYield 69.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (1.20 ml, 12.7 mmol) was added to a stirred solution of cis-methyl 3-aminocyclohexanecarboxylate (0.40 g, 2.54 mmol) in pyridine (10 ml) under an atmosphere of argon and stirred for 3 h at room temperature. The excess pyridine was removed under vacuo and the resulting residue was partitioned between DCM and saturated sodium bicarbonate solution. The separated organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuo to afford cis-methyl 3-acetamidocyclohexanecarboxylate (350 mg, 69.0%) as a colorless liquid.

Workup

  1. customThe excess pyridine was removed under vacuo
  2. customthe resulting residue was partitioned between DCM and saturated sodium bicarbonate solution
  3. washThe separated organic layer was washed with water, brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuo

Sources & evidence

ORD record
ord-8aaa3d894a524892b3e55f92373b0d03
Source dataset
uspto-grants-2015_06
Patent number
US09067888B2

Reaction notes

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