Ammonium Hydroxide → 2-(3-Aminooxetan-3-yl)acetamide

HRID 1480118Notes

Reaction equation

HRID 1480118 reaction equation
[NH2:1][C:2]1([CH2:6][C:7]([O:9]CC)=O)[CH2:5][O:4][CH2:3]1.[OH-].[NH4+:13]>C1(C)C=CC=CC=1>[NH2:1][C:2]1([CH2:6][C:7]([NH2:13])=[O:9])[CH2:5][O:4][CH2:3]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 55280628Ethyl 2-(3-aminooxetan-3-yl)acetate

Product 1

HCID 755375242-(3-Aminooxetan-3-yl)acetamideYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a microwave tube was added ethyl 2-(3-aminooxetan-3-yl)acetate (CAN 1207175-54-9, 400 mg, 2.51 mmol) followed by toluene (8.0 ml) and 25% ammonium hydroxide (7.2 g, 8.0 ml, 51.4 mmol). The tube was sealed and the reaction mixture was stirred vigorously at room temperature for 6 days. The reaction mixture was concentrated in vacuo and azeotroped several times with 20 ml toluene. The crude solid was dried under high-vacuum at 40° C. to dryness to yield the title compound (290 mg, 89%) as a white solid. MS (ESI, m/z): 131.1 (M+H+).

Workup

  1. customThe tube was sealed
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customazeotroped several times with 20 ml toluene
  4. customThe crude solid was dried under high-vacuum at 40° C. to dryness

Sources & evidence

ORD record
ord-e9fbb2c7ebf247a8b4649ac50315a79a
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

Loading…