Acetic Anhydride → HCID 131730828, compound

HRID 1896266Notes

Reaction equation

HRID 1896266 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 67070431HCID 67070431, compound

Product 1

HCID 131730828HCID 131730828, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Acetic anhydride (1.20 ml, 12.7 mmol) was added to a solution of trans-methyl 3-aminocyclohexane-carboxylate (0.40 g, 2.54 mmol) in pyridine (10 ml) at 0° C. The reaction mixture was warmed to room temperature and stirred for 1 h. The volatiles were removed in vacuum, the resulting residue was dissolved in DCM and washed with saturated sodium bicarbonate solution followed by brine solution (10 ml). After drying over anhydrous sodium sulfate and filtration the filtrate was concentrated under vacuum to afford 350 mg (69.0%) of trans-methyl 3-acetamidocyclohexanecarboxylate as a colorless liquid.

Workup

  1. customThe volatiles were removed in vacuum
  2. dissolutionthe resulting residue was dissolved in DCM
  3. washwashed with saturated sodium bicarbonate solution
  4. dry with materialAfter drying over anhydrous sodium sulfate and filtration the filtrate
  5. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-cd74a92e6a434c12882910a78e2ba383
Source dataset
uspto-grants-2013_08
Patent number
US08518948B2

Reaction notes

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