Methyl iodide → 2-Adamantan-1-ylmethyl-1-methyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

HRID 1018305Notes

Reaction equation

HRID 1018305 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[NH:8][C:7]=1[CH2:17][C:18]12[CH2:27][CH:22]3[CH2:23][CH:24]([CH2:26][CH:20]([CH2:21]3)[CH2:19]1)[CH2:25]2)=[O:5])[CH3:2].[H-].[Na+].I[CH3:31]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:8]([CH3:31])[C:7]=1[CH2:17][C:18]12[CH2:27][CH:22]3[CH2:21][CH:20]([CH2:26][CH:24]([CH2:23]3)[CH2:25]1)[CH2:19]2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 117175262-Adamantan-1-ylmethyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl ester

Product 1

HCID 701183052-Adamantan-1-ylmethyl-1-methyl-5-phenyl-1h-pyrrole-3-carboxylic acid ethyl esterYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-adamantan-1-ylmethyl-5-phenyl-1H-pyrrole-3-carboxylic acid ethyl ester (Example 1, step b) (726 mg, 2.00 mmol) in DMF (3 ml) was added sodium hydride (60% dispersion in oil) (100 mg, 2.50 mmol) in small portions at 0° C. The mixture was stirred at room temperature for 30 min, then iodomethane (1.00 ml, 16.0 mmol) was added and the stirring was continued for 1 h. The reaction mixture was partitioned between ethyl acetate and 1M hydrochloric acid, the organic layer was washed with water, dried, and the solvent was evaporated to afford the product as a white solid (620 mg, 82%). 1H NMR (300 MHz, CDCl3) 7.35 (5H, m), 6.64 (1H, s), 4.27 (2H, q), 3.51 (3H, s), 2.80 (2H, br s), 1.96 (3H, br s), 1.64 (12H, m), 1.35 (3H, t).

Workup

  1. waitthe stirring was continued for 1 h
  2. customThe reaction mixture was partitioned between ethyl acetate and 1M hydrochloric acid
  3. washthe organic layer was washed with water
  4. customdried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4e4d0dcb8dce4745a380b4d5a671e958
Source dataset
uspto-grants-2002_11
Patent number
US06479531B1

Reaction notes

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