4-Tert-Butylaniline → HCID 67236768, compound

HRID 2364802Notes

Reaction equation

HRID 2364802 reaction equation
CS(O[CH:6]([C:24]1[CH:29]=[CH:28][C:27]([Br:30])=[CH:26][CH:25]=1)[CH2:7][CH2:8][CH:9](OS(C)(=O)=O)[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)(=O)=O.[C:31]([C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1)([CH3:34])([CH3:33])[CH3:32]>CN(C=O)C>[Br:30][C:27]1[CH:28]=[CH:29][C:24]([CH:6]2[CH2:7][CH2:8][CH:9]([C:10]3[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=3)[N:39]2[C:38]2[CH:40]=[CH:41][C:35]([C:31]([CH3:34])([CH3:33])[CH3:32])=[CH:36][CH:37]=2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 698614-Tert-ButylanilineHCID 58226750HCID 58226750, compound

Product 1

HCID 67236768HCID 67236768, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The product from Example 39C (10.86 g, 20.79 mmol), DMF (65 mL) and 4-tert-butylaniline (26.5 mL, 166 mmol) was reacted according to the procedure in Example 39D to provide the title compound (5.0 g, 50%, yellow solid) as a mixture of cis and trans pyrrolidine stereoisomers.

Sources & evidence

ORD record
ord-7052e276eda047b48db20ed331317d2c
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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