1,2-Dichloroethane → N-methoxy-N-methylcyclobutanecarboxamide

HRID 1475500Notes

Reaction equation

HRID 1475500 reaction equation
Cl.[CH3:2][O:3][NH:4]OOC.[CH3:8]CN(C(C)C)C(C)C.[CH:17]1([C:21]([OH:23])=O)[CH2:20][CH2:19][CH2:18]1.C(Cl)CCl>C(Cl)Cl>[CH3:2][O:3][N:4]([CH3:8])[C:21]([CH:17]1[CH2:20][CH2:19][CH2:18]1)=[O:23]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 19494Cyclobutanecarboxylic acidHCID 81531DiisopropylethylamineHCID 22015712N,O-dimethoxyhydroxylamine hydrochloride

Product 1

HCID 45084194N-methoxy-N-methylcyclobutanecarboxamideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cooled suspension of N,O-dimethoxyhydroxylamine hydrochloride (1.95 g, 20 mmol) in DCM (50 mL) was added DIPEA (7.0 mL, 40.0 mmol) and cyclobutanecarboxylic acid (1.9 mL, 20 mmol). After stirring for 5 min, EDC (4.2 g, 22.0 mmol) was added and the reaction mixture was stirred overnight while allowing it to warm to room temperature. The mixture was diluted with DCM (50 mL) and was transferred to a separatory funnel. The organic layer was washed with saturated aqueous NaHCO3 (2×50 mL), water (1×50 mL), brine (50 mL), dried (MgSO4) and concentrated. Chromatography (SiO2, eluted with petrol-EtOAc 0-40%) gave the title compound (1.9 g, 67%) as an oil. MS: [M+H]+=144.

Workup

  1. stirringthe reaction mixture was stirred overnight
  2. customwas transferred to a separatory funnel
  3. washThe organic layer was washed with saturated aqueous NaHCO3 (2×50 mL), water (1×50 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washChromatography (SiO2, eluted with petrol-EtOAc 0-40%)

Sources & evidence

ORD record
ord-c08b4928d02847f5b516ef9a91db36db
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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