Trityl chloride → N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

HRID 234745Notes

Reaction equation

HRID 234745 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH2:5]3)[CH:3]1[NH2:12])[CH2:9]2.[C:13]1([C:19](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>ClCCl>[C:19]([NH:12][CH:3]1[CH:4]2[CH2:5][CH:6]3[CH2:7][CH:8]([CH2:9][C:2]1([OH:1])[CH2:11]3)[CH2:10]2)([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 6456Trityl chloride2×HCID 124667122-Aminoadamantan-1-ol

Product 1

HCID 54340516N-trityl-1-hydroxytricyclo[3.3.1.13,7]decan-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (0.47 g; 0.0028 mole), [prepared via a procedure of W. V. Curran and R. B. Angier, J. of Org. Chem., 34(11), 3668-70 (1969)] in dichloromethane (45 ml)is added triphenylmethyl chloride (0.78 g; 0.0028 mole) in dichloromethane (5 ml). This mixture is refluxed for 7 hours and then more triphenylmethyl chloride (0.35 g) is added and the reaction refluxed overnight. The reaction is stripped to dryness and the products separated via flash chromatography (eluted with 25% ethyl acetate/hexane) to obtain N-trityl-1-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine which is used directly in step B.

Workup

  1. temperatureThis mixture is refluxed for 7 hours
  2. temperaturethe reaction refluxed overnight
  3. customthe products separated via flash chromatography (eluted with 25% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5aacd6119b2f466d9ff0e62f15ad79b8
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

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