Triethylamine → 1-(4-Formylphenyl)azetidine-3-carboxylic acid
Reaction equation
F[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[NH:10]1[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11]1.C(N(CC)CC)C>CS(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([N:10]2[CH2:13][CH:12]([C:14]([OH:16])=[O:15])[CH2:11]2)=[CH:3][CH:4]=1)=[O:7]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
To a stirred solution of 4-fluoro benzaldehyde (5 g, 40.28 mmol) in DMSO (70 mL) was added azetidine-3-carboxylic acid (8.14 g, 80.56 mmol) followed by addition of triethyl amine (20.38 g, 201.41 mmol) at room temperature. Resulting reaction mixture was heated at 100° C. for 24 hours under nitrogen atmosphere. After complete consumption of starting material, reaction mixture was cooled to room temperature and quenched with ice cold water (150 mL). Aqueous layer was extracted with EtOAc (3×150 mL). Combined organic layer was washed with water (2×300 mL), dried over sodium sulphate; filtered and evaporated in vacuo to afford brown colored solid (4 g, 48%). 1H NMR (400 MHz, DMSO-d6) δ: 3.54-3.59 (m, 1H), 4.03 (t, 2H, J=6.8 Hz), 4.16 (t, 2H, J=8.36 Hz), 6.52 (d, 2H, J=8.36 Hz), 7.69 (d, 2H, J=8.6 Hz), 9.68 (s, 1H); LC-MS (M−H): =203.70
Workup
- customResulting
- customreaction mixture
- customAfter complete consumption of starting material, reaction mixture
- temperaturewas cooled to room temperature
- customquenched with ice cold water (150 mL)
- extractionAqueous layer was extracted with EtOAc (3×150 mL)
- washCombined organic layer was washed with water (2×300 mL)
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated in vacuo
Sources & evidence
- ORD record
- ord-6a90dc96c85040aa9cd17981d521fea1
- Source dataset
- uspto-grants-2015_06
- Patent number
- US09061013B2
Reaction notes
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