Sodium Hydroxide → [(1S,4R)-4-(2-amino-6-butoxy-purin-9-yl)cyclopent-2-en-1-yl]methanol

HRID 728647

Reaction equation

HRID 728647 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]2)=[C:6](Cl)[N:5]=1.[OH-:21].[Na+]>>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C@@H:13]2[CH2:17][C@H:16]([CH2:18][OH:19])[CH:15]=[CH:14]2)=[C:6]([O:21][CH2:17][CH2:13][CH2:14][CH3:15])[N:5]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468291[(1S,4R)-4-(2-amino-6-butoxy-purin-9-yl)cyclopent-2-en-1-yl]methanol

Procedure

A flask was charged with sodium hydride (60% oil dispersion 300 mg, 7.5 mmol) which was then washed with hexanes before the addition of butanol (10 mL) containing (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (800 mg, 3 mmol) from Example 4. The solution was stirred at reflux for 2 hours and then neutralized by the addition of 1.0 N NaOH. Concentration of the solution afforded the crude product which was purified by elution from a silica gel column with 5% methanol-chloroform; (810 mg, 94%). Crystallization of such a sample from ethanol/acetonitrile gave an off-white powder, m.p. 122-123° C.

Workup

  1. washwas then washed with hexanes before the addition of butanol (10 mL)
  2. temperatureat reflux for 2 hours

Sources & evidence

ORD record
ord-b093364cb8e4422293f8a37da85ec685
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Linked notes

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