Water → 1-Methoxycyclopentanecarboxamide

HRID 626535Notes

Reaction equation

HRID 626535 reaction equation
[CH3:1][O:2][C:3]1([C:8]([OH:10])=O)[CH2:7][CH2:6][CH2:5][CH2:4]1.C1N=C[N:13](C(N2C=NC=C2)=O)C=1.[NH4+].[OH-].O>CCOC(C)=O>[CH3:1][O:2][C:3]1([C:8]([NH2:13])=[O:10])[CH2:7][CH2:6][CH2:5][CH2:4]1

Participants

6

Reactant 4

HCID 962WaterHCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 205670831-Methoxycyclopentane-1-carboxylic acid

Product 1

HCID 675281901-MethoxycyclopentanecarboxamideYield 101%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-methoxycyclopentanecarboxylic acid (0.9 g, 6.24 mmol) in EtOAc (30 mL) was treated with CDI (1.316 g, 8.12 mmol), stirred at RT for 0.5 h, treated with NH4OH (˜15M, 0.729 mL, ˜10.9 mmol) and stirred at RT overnight. The mixture was treated with water, extracted with EtOAc (3×) and the combined organics were washed with brine, dried over Na2SO4 and concentrated to dryness to afford 1-methoxycyclopentanecarboxamide (900 mg, 101%). 1H NMR (400 MHz, CDCl3): δ 6.45 (br s, 1H), 5.42 (br s, 1H), 3.24 (s, 3H), 2.07-2.04 (m, 2H), 1.90-1.87 (m, 2H), 1.75-1.73 (m, 4H).

Workup

  1. stirringstirred at RT overnight
  2. extractionextracted with EtOAc (3×)
  3. washthe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-97746579b0ac4d3790cd177d5ca58892
Source dataset
uspto-grants-2016_04
Patent number
US09309224B2

Reaction notes

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