Trityl chloride → HCID 54523384, compound

HRID 234743

Reaction equation

HRID 234743 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([NH2:12])([CH2:5]3)[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][C:4]12[CH2:10][CH:8]3[CH2:7][CH:6]([CH2:11][C:2]([OH:1])([CH2:9]3)[CH2:3]1)[CH2:5]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 6586453-Amino-1-adamantanol

Product 1

HCID 54523384HCID 54523384, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-hydroxytricyclo[3.3.1.13,7 ]decan-1-amine (5 g; 0.03 mole) dissolved in dichloromethane (140 ml) with gentle heating is added triethylamine (6 g; 0.06 mole) and cooled in an ice bath. Triphenylmethyl chloride (8.30 g; 0.03 mole) in CH2Cl2 (10 ml) is added all at once. The reaction is stirred in an ice bath for 10 minutes, warmed to room temperature and then refluxed for 3 hours. The reaction is then filtered and the filtrate evaporated to dryness. The reaction products are separated on HPLC, using 15% ethyl acetate/hexane and the product is then recrystallized from ethyl acetate/pet. ether to give N-trityl-3-hydroxytricyclo-[3.3.1.13,7 ]decan-1-amine (m.p. 184°-186° C.) which is used directly in step C.

Workup

  1. temperaturewith gentle heating
  2. temperaturecooled in an ice bath
  3. temperaturerefluxed for 3 hours
  4. filtrationThe reaction is then filtered
  5. customthe filtrate evaporated to dryness
  6. customThe reaction products are separated on HPLC
  7. customthe product is then recrystallized from ethyl acetate/pet. ether

Sources & evidence

ORD record
ord-c0273586d2bd400cb938da500fbeba96
Source dataset
uspto-grants-1997_01
Patent number
US05596020

Linked notes

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