Hydrochloric Acid → 3-hydroxy-N-methoxy-N-methylcyclobutanecarboxamide

HRID 1966164Notes

Reaction equation

HRID 1966164 reaction equation
[CH3:1][O:2][N:3]([CH3:11])[C:4]([CH:6]1[CH2:9][C:8](=[O:10])[CH2:7]1)=[O:5].CO.[BH4-].[Na+].Cl>>[OH:10][CH:8]1[CH2:9][CH:6]([C:4]([N:3]([O:2][CH3:1])[CH3:11])=[O:5])[CH2:7]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 4311764Sodium borohydrideHCID 86634348N-methoxy-N-methyl-3-oxocyclobutanecarboxamide

Product 1

HCID 186915573-hydroxy-N-methoxy-N-methylcyclobutanecarboxamideYield 146.6%

Procedure

N-Methoxy-N-methyl-3-oxocyclobutanecarboxamide (1 g, 0.006 mol) was dissolved in methanol (8 mL, 0.2 mol). To the mixture, sodium borohydride (0.2 g, 0.006 mol) was added. The reaction was stirred at rt for 1 h. To the reaction mixture was added 1N aq. HCl to adjust the pH to 2. The mixture was concentrated, then extracted with EtOAc. The combined organic layers were dried over MgSO4 and concentrated to give crude product (1.4 g) as light yellow oil. LCMS calculated for C7H14NO3(M+H)+: 160.0. Found: 160.3.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f6d69ab6914d48fd837fdeb5e79fe91b
Source dataset
uspto-grants-2013_04
Patent number
US08420629B2

Reaction notes

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