HCID 59605965, compound → HCID 59605642, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH2:13][CH2:14][O:15][CH2:16][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3-(3,6-dihydro-2H-pyran-4-yl)azetidine-1-carboxylic acid tert-butyl ester (28.6 g, 0.12 mol) and 10% palladium on charcoal (5.0 g) in IMS (500 mL) was stirred under hydrogen (4 bar) at room temperature for 36 hours. The reaction mixture was filtered through a bed of Celite® which was washed with IMS. The filtrates were combined and concentrated to give a residue which was reacted as above for 18 hours. The reaction mixture was worked up as above to give a residue which was dried under reduced pressure to give 3-(Tetrahydropyran-4-yl)azetidine-1-carboxylic acid tert-butyl ester as a beige solid (26.7 g, 92%). 1H NMR (300 MHz, CHCl3-d): δ 4.03-3.90 (m, 4 H); 3.63 (dd, J=8.6, 5.7 Hz, 2 H); 3.37 (td, J=11.8, 2.0 Hz, 2 H); 2.32-2.19 (m, 1 H); 1.63-1.48 (m, 3 H); 1.44 (s, 9 H); 1.29-1.12 (m, 2 H).