Trityl chloride → N-trityl-5-hydroxytricyclo[3.3.1.13,7]decan-2-amine

HRID 234737Notes

Reaction equation

HRID 234737 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:4]([CH:5]3[NH2:12])[CH2:3]1)[CH2:9]2.C(N(CC)CC)C.[C:20]1([C:26](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:26]([NH:12][CH:5]1[CH:4]2[CH2:10][CH:8]3[CH2:9][C:2]([OH:1])([CH2:11][CH:6]1[CH2:7]3)[CH2:3]2)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 28574474-Aminoadamantan-1-ol

Product 1

HCID 54395449N-trityl-5-hydroxytricyclo[3.3.1.13,7]decan-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (2.0 g; 0.012 mole) is dissolved in 70 ml of dichloromethane with gentle heating. To this is added triethylamine (2.4 g; 0.024 mole) and cooled in an ice bath. To this is added triphenylmethyl chloride (3.34 g; 0.012 mole) in dichloromethane (10 ml) all at once. The reaction is stirred for 10 minutes with ice cooling and then 5 hours at room temperature. The reaction mixture is heated to reflux overnight, cooled, filtered and evaporated to dryness. Purification is accomplished via HPLC (eluting with 20% ethyl acetate/hexane) to obtain N-trityl-5-hydroxytricyclo[3.3.1.13,7 ]decan-2-amine (m.p. 166°-170° C.) which is used directly in step E.

Workup

  1. temperaturecooled in an ice bath
  2. custom5 hours
  3. customat room temperature
  4. temperatureThe reaction mixture is heated
  5. temperatureto reflux overnight
  6. temperaturecooled
  7. filtrationfiltered
  8. customevaporated to dryness
  9. customPurification
  10. washis accomplished via HPLC (eluting with 20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bd3fadbeba734818906495345faaa90b
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Reaction notes

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