Trityl chloride → HCID 54023768, compound

HRID 2399738Notes

Reaction equation

HRID 2399738 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[OH:7].[C:8]1([C:14](Cl)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(N(CC)CC)C>C(Cl)Cl>[C:8]1([C:14]([NH:1][C@@H:2]2[CH2:6][CH2:5][CH2:4][C@H:3]2[OH:7])([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-ol

Product 1

HCID 54023768HCID 54023768, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of trans-2-aminocyclopentanol (45.84 mmol), triphenylmethylchloride (11.50 g; 41.26 mmol) and triethylamine (15.97 ml; 114.60 mmol) in 100 ml CH2Cl2 is refluxed overnight. The reaction mixture is cooled and concentrated in vacuo and flash chromatographed using 5:1; hexane:EtOAc to obtain trans-2-triphenylmethylaminocyclopentanol which is used directly in the next step.

Workup

  1. temperatureis refluxed overnight
  2. temperatureThe reaction mixture is cooled
  3. concentrationconcentrated in vacuo and flash
  4. customchromatographed

Sources & evidence

ORD record
ord-c7e32127b3354af38fc8f8dd93103490
Source dataset
uspto-grants-1995_09
Patent number
US05451596

Reaction notes

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