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

HRID 1018305
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반응식

HRID 1018305 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4e4d0dcb8dce4745a380b4d5a671e958
출처 데이터셋
uspto-grants-2002_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06479531B1

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