Trityl chloride → HCID 67490778, compound

HRID 1917397Notes

Reaction equation

HRID 1917397 reaction equation
C(N(CC)CC)C.[C:8](Cl)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[NH2:28][CH2:29][C:30]1[O:31][CH2:32][CH2:33][CH2:34][CH:35]=1>ClCCl>[C:8]([NH:28][CH2:29][C:30]1[O:31][CH2:32][CH2:33][CH2:34][CH:35]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 785082H-Pyran, 3,4-dihydro-2-aminomethyl-

Product 1

HCID 67490778HCID 67490778, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (37.7 mL, 270 mmol) and trityl chloride (41.4 g, 149 mmol) were sequentially added to a solution of the crude 2-aminomethyl-5,6-dihydro-4H-pyran (about 193 mmol) in dichloromethane (500 mL), and the mixture was stirred at room temperature for 11 hours. The reaction solution was diluted with dichloromethane (500 mL), washed with water (2×500 mL) and brine (500 mL), and then dried over anhydrous sodium sulfate and filtered. The solvent was evaporated under reduced pressure. Then, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95→10:90) to give 22.2 g (four steps, 32%) of the title compound as a colorless transparent gummy solid.

Workup

  1. washwashed with water (2×500 mL) and brine (500 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customThen, the residue was purified by silica gel column chromatography (ethyl acetate:hexane=5:95→10:90)

Sources & evidence

ORD record
ord-49c42ef7dbc84fb0bb486257cb09fa1d
Source dataset
uspto-grants-2013_12
Patent number
US08618094B2

Reaction notes

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