Hydrochloric Acid → HCID 67051866, compound

HRID 1809017Notes

Reaction equation

HRID 1809017 reaction equation
[OH:1][C:2]1([CH:13]([N+:15]([O-:17])=[O:16])[CH3:14])[CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[ClH:18]>CO.O1CCOCC1>[ClH:18].[N+:15]([CH:13]([C:2]1([OH:1])[CH2:5][NH:4][CH2:3]1)[CH3:14])([O-:17])=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67051851HCID 67051851, compound

Product 1

HCID 67051866HCID 67051866, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1,1-Dimethylethyl 3-hydroxy-3-(1-nitroethyl)azetidine-1-carboxylate was dissolved in methanol (5 mL) and treated with 4 N HCl in dioxane. The solution was briefly heated to reflux and then was concentrated in vacuo to afford 178 mg, 0.98 mmol (96%) of 3-(1-nitroethyl)azetidin-3-ol hydrochloride as a white solid. 1H NMR (400 MHz, DMSO): 9.30 (br s, 1H), 8.96 (br s, 1H), 5.12 (q, 1H), 4.44-4.38 (m, 1H), 4.22-4.17 (m, 1H), 3.94-3.87 (m, 1H), 3.85-3.77 (m, 1H), 1.44 (d, 3H).

Workup

  1. temperatureThe solution was briefly heated
  2. temperatureto reflux
  3. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-da1d98f2a54240d0a79f1b5034cb9a42
Source dataset
uspto-grants-2013_01
Patent number
US08362002B2

Reaction notes

Loading…