Aniline → HCID 58504736, compound

HRID 2367263Notes

Reaction equation

HRID 2367263 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]([OH:15])=O)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].C1N=CN(C(N2C=NC=C2)=O)C=1.[CH:28]1[CH:29]=[CH:30][C:31]2N(O)N=[N:34][C:32]=2[CH:33]=1.NC1C=CC=CC=1>C(Cl)Cl.CCN(C(C)C)C(C)C>[C:32]1([NH:34][C:13]([CH:10]2[CH2:11][CH2:12][N:8]([C:6]([O:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])[CH2:9]2)=[O:15])[CH:33]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

7

Reactant 4

HCID 6115AnilineHCID 682631,1'-CarbonyldiimidazoleHCID 757711-HydroxybenzotriazoleHCID 27605291-((Tert-butoxy)carbonyl)pyrrolidine-3-carboxylic acid

Product 1

HCID 58504736HCID 58504736, compoundYield 121%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 81531DiisopropylethylamineSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinecarboxylic acid (1.0 g, 4.7 mmol), CDI (1.3 g, 7.0 mmol) and HOBT (0.5 g) in CH2Cl2 (20 mL) and Hunig's base (2.0 mL) was cooled to 0° C. and stirred for 15 minutes. Then aniline (520 mg, 5.6 mmol) was added and the reaction mixture was stirred at room temperature for 6 hours. The mixture was concentrated and purified by SiO2 chromatography (eluent: 1:1 EtOAc:petroleum ether) to afford the title compound (1.3 g) as an oil. 1H NMR (400 MHz, CDCl3): δ 1.40 (s, 9H), 2.10 (m, 2H), 3.0 (m, 1H), 3.7-4 (m, 4H), 4.2 (m, 1H), 7.21 (m, 1H), 7.40 (m, 2H), 7.51 (m, 1H).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 6 hours
  2. concentrationThe mixture was concentrated
  3. custompurified by SiO2 chromatography (eluent: 1:1 EtOAc:petroleum ether)

Sources & evidence

ORD record
ord-d625247caf8f467eba9243c5e6b59391
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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