Cyclooctylamine → HCID 86744925, compound

HRID 1534397Notes

Reaction equation

HRID 1534397 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. additionwas added
  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-2dd13c78a9f6490f962a723b33300418
Source dataset
uspto-grants-1992_02
Patent number
US05089500

Reaction notes

Loading…