Pyrrolidine → HCID 67283988, compound

HRID 2111678Notes

Reaction equation

HRID 2111678 reaction equation
C(O[C:4]([C:6]1[CH:10]=[C:9]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[O:8][N:7]=1)=[O:5])C.[NH:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1>>[N:20]1([C:4]([C:6]2[CH:10]=[C:9]([CH2:11][NH:12][C:13]([O:15][C:16]([CH3:17])([CH3:18])[CH3:19])=[O:14])[O:8][N:7]=2)=[O:5])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 10588096Ethyl 5-(N-Boc)aminomethylisoxazole-3-carboxylate

Product 1

HCID 67283988HCID 67283988, compoundYield 79%

Conditions

Temperature
85 °C

Procedure

3-Ethoxycarbonyl-5-[N-(tert-butyloxycarbonyl)aminomethyl]isoxazole (Method 73; 500 mg, 1.85 mmol) was dissolved in pyrrolidine (4 ml) and the mixture heated for 3 hours at 85° C. The volatiles were removed by evaporation and the residue was triturated with diethyl ether to give the title compound (432 mg, 79%) as a white solid. NMR (DMSO): 1.38 (s, 9H), 1.85 (m, 4H), 3.50 (t, 2H), 3.62 (t, 2H), 4.29 (d, 2H), 6.47 (1H), 7.53 (s, 1H); m/z 240 (M-C4H8)+.

Workup

  1. customThe volatiles were removed by evaporation
  2. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-fc0badb1b6fd4a778d5dae888f9321cb
Source dataset
uspto-grants-2009_04
Patent number
US07521453B2

Reaction notes

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