HCID 57470079, compound → tert-Butyl 3-(4-aminophenyl)azetidine-1-carboxylate

HRID 592344Notes

Reaction equation

HRID 592344 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-])=O)=[CH:14][CH:13]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCOC(C)=O.[Pd]>[NH2:18][C:15]1[CH:14]=[CH:13][C:12]([CH:10]2[CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:11]2)=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 57470079HCID 57470079, compound

Product 1

HCID 56956222tert-Butyl 3-(4-aminophenyl)azetidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 10% Pd/C (0.320 g) and tert-butyl-3-(4-nitrophenyl)azetidine-1-carboxylate (I6) (2.14 g, 7.68 mmol) in EtOAc (16 mL) was stirred under a hydrogen atmosphere for 18 hours. Additional 10% Pd/C (1.00 g) was added and stirring continued for a further 20 hours. The resulting mixture was filtered through a pad of Celite, washing with EtOAc, and the filtrate concentrated in vacuo to give the title compound I7 as a light yellow/cream solid (1.80 g, 94%); 1H NMR (300 MHz, CDCl3) δ 7.12 (d, J=8.3 Hz, 2H), 6.69 (dd, J=6.5, 1.9 Hz, 2H), 4.29 (t, J=8.7 Hz, 2H), 3.93 (dd, J=8.4, 6.1 Hz, 2H), 3.65 (brs, 2H), 1.55-1.68 (m, 1H), 1.48 (s, 9H). LCMS-B: rt 4.964 min; m/z 249 [M+H]+.

Workup

  1. stirringstirring
  2. waitcontinued for a further 20 hours
  3. filtrationThe resulting mixture was filtered through a pad of Celite
  4. washwashing with EtOAc
  5. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-8670e57467fd4723852608bd44eaf6a0
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

Loading…