Cyclooctylamine → HCID 86744925, compound

HRID 1087036Notes

Reaction equation

HRID 1087036 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[CH:19]1([NH2:27])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[CH2:15][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:27][CH:19]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:3]=1

Participants

5

Reactant 3

HCID 2903CyclooctylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 86744925HCID 86744925, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(±)-cis-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.549 g, 2 mmol), cyclooctylamine (0.762 g, 6 mmol) and ethanol (15 mL) were stirred at reflux under nitrogen for 20 hours. 1N NaOH (2 mL) was added and solvent was evaporated. The residual oil was chromatographed on silica gel. Title compound was eluted with 5% methanol-chloroform as white powder after crystallization from acetonitrile-methanol (0.623 g, 87%); m.p. 171°-173° C.

Workup

  1. temperatureat reflux under nitrogen for 20 hours
  2. customsolvent was evaporated
  3. customThe residual oil was chromatographed on silica gel
  4. washTitle compound was eluted with 5% methanol-chloroform as white powder
  5. customafter crystallization from acetonitrile-methanol (0.623 g, 87%)

Sources & evidence

ORD record
ord-1b75932b7f9e469b91ba91ccb01dd9f8
Source dataset
uspto-grants-1991_07
Patent number
US05034394

Reaction notes

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