Formic Acid → 4-Formylmorpholine-3-carboxylic acid
Reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8].[CH:10](O)=[O:11].C(OC(=O)C)(=O)C>O>[CH:10]([N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[C:7]([OH:9])=[O:8])=[O:11]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 2.5 °C
Procedure
To a mixture of morpholine-3-carboxylic acid (5 g, 38.1 mmol) and formic acid (46.6 g, 1.01 mol) cooled at 0-5° C. was added acetic anhydride (26.7 g, 262 mmol) dropwise. The resulting mixture was stirred at room temperature for 2 h. An excess of water was added while cooling the mixture. The resulting mixture was then concentrated under reduced pressure. The crude product 4-formyl-morpholine-3-carboxylic acid (6 g) was used in the next step without further purification. LC/MS (method 7): Rt=0.13 min; m/z=160.1 (M+H+).
Workup
- temperaturewhile cooling the mixture
- concentrationThe resulting mixture was then concentrated under reduced pressure
- customThe crude product 4-formyl-morpholine-3-carboxylic acid (6 g) was used in the next step without further purification
Sources & evidence
- ORD record
- ord-0be6712826f34056b9e1d39b23a97a1f
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284333B2
Reaction notes
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