Trityl chloride → HCID 178521610, compound

HRID 605849Notes

Reaction equation

HRID 605849 reaction equation
[NH2:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1.C(N(CC)CC)C.[C:16](Cl)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[C:16]([NH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([OH:8])[CH2:4][CH2:3]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 178511715HCID 178511715, compound

Product 1

HCID 178521610HCID 178521610, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trans-4-aminocyclohexanol (2.6 g, 22.6 mmol) was suspended in 60 mL DCM, then 4 mL (28.7 mmol) triethylamine was added. The mixture was cooled in ice bath, and trityl chloride (6.3 g, 22.6 mmol) was added. The mixture was stirred overnight, allowing it to slowly warm up. Saturated NaHCO3 was added to quench the chloride, and product was extracted with EtOAc three times. The combined organic layer was washed with brine, and dried over Na2SO4. Column chromatography with 20-40% EtOAc in hexanes provided 5.3 g (66%) white solid.

Workup

  1. temperatureThe mixture was cooled in ice bath
  2. temperatureto slowly warm up
  3. customto quench the chloride, and product
  4. extractionwas extracted with EtOAc three times
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4

Sources & evidence

ORD record
ord-464e5603b15a455681e477496affb459
Source dataset
uspto-grants-2011_03
Patent number
US07915268B2

Reaction notes

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