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

HRID 728646

Reaction equation

HRID 728646 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.[CH:21]([OH:24])([CH3:23])[CH3:22]>>[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:24][CH:21]([CH3:23])[CH3:22])[N:5]=1

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 468293[(1S,4R)-4-(2-amino-6-isopropoxy-purin-9-yl)cyclopent-2-en-1-yl]methanol

Conditions

Temperature
75 °C

Procedure

A flask was charged with sodium hydride (60% oil dispersion, 240 mg, ~6 mmol) which was washed with hexanes before the addition of isopropanol (20 mL) and (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.318 g, 1.19 mmol) from Example 4. This solution was heated at 75° C. for 2 hours before being allowed to cool to room temperature and neutralized by addition of 1.0 N HC1. The solution was concentrated and the residue was placed on a silica gel column which was eluted with 10% methanol-chloroform. Crystallization from ethanol:water 1:1 yielded off-white crystals (265 mg, 77%), m.p. 188-191° C.

Workup

  1. temperatureto cool to room temperature
  2. additionneutralized by addition of 1.0 N HC1
  3. concentrationThe solution was concentrated
  4. washwas eluted with 10% methanol-chloroform
  5. customCrystallization from ethanol:water 1:1 yielded off-white crystals (265 mg, 77%), m.p. 188-191° C.

Sources & evidence

ORD record
ord-d324202755b44d0292f3e65082ac01d7
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Linked notes

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