Methyl iodide → {2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester

HRID 705967Notes

Reaction equation

HRID 705967 reaction equation
[C:1]([O:5][C:6](=[O:24])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH3:27]I>C1COCC1>[C:1]([O:5][C:6](=[O:24])[N:7]([CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)=[CH:12][CH:11]=1)[CH3:27])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 67776301{2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 67773542{2-[4-(4-Fluoro-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl esterYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

{2-[4-(4-fluoro-phenoxy)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3.018 mmol, 1 eq) was dissolved in dry THF (30 ml) and NaH (3.621 mmol, 1.2 eq) was added. After 30 min, the reaction mixture was treated with methyl iodide (30.176 mmol, 10 eq) and was stirred overnight. After overnight the excess NaH was quenched by a slow addition of water, diluted with brine (30 ml) and extracted with Et2O (3×20 ml). Combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to give a product without further purification {2-[4-(4-fluoro-phenoxy)-phenyl]-ethyl}-methyl-carbamic acid tert-butyl ester (1.592 mmol, yield=53%, purity=97%). [M+H]+=272.28 1H NMR (300 MHz, CDCl3) δ/ppm 1.55 (s, 9H), 7.24 (m, 5H), 3.39 (br. s., 2H), 6.83-7.03 (m, 5H), 7.06-7.17 (m, 2H), 7.24 (s, 2H)

Workup

  1. customAfter overnight the excess NaH was quenched by a slow addition of water
  2. additiondiluted with brine (30 ml)
  3. extractionextracted with Et2O (3×20 ml)
  4. dry with materialCombined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give a product

Sources & evidence

ORD record
ord-d788ace6d0c44a8a9397a5daffd81c2b
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

Loading…