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

HRID 1779040Notes

Reaction equation

HRID 1779040 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:13][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:11]2)=[CH:6][CH:5]=1)([O-])=O>CCOC(C)=O.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:11][N:12]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:13]2)=[CH:8][CH:9]=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 tert-butyl 3-(4-nitrophenyl)azetidine-1-carboxylate (A76) (2.14 g, 7.68 mmol) and 10% Pd/C (0.320 g) in EtOAc (16 mL) was stirred under a hydrogen atmosphere for 18 hours. Additional 10% Pd/C (1.00 g) was added and the mixture stirred under a hydrogen atmosphere 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 A77 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), 3.69-3.61 (s, 2H), 1.55-1.68 (m, 1H), 1.48 (s, 9H). LCMS-B: rt 4.964 min; m/z 249 [M+H]+.

Workup

  1. stirringthe mixture stirred under a hydrogen atmosphere for a further 20 hours
  2. filtrationThe resulting mixture was filtered through a pad of Celite
  3. washwashing with EtOAc
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-2423f923a28c4cbe89d2b9267876a8de
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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