rac-(1R,2R)-2-aminocyclopentan-1-ol → N-(trans-2-Hydroxycyclopentyl)-2-methyladenosine

HRID 1086802Notes

Reaction equation

HRID 1086802 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:12]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]1[OH:14].[NH2:21][C@@H:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[OH:27]>C(O)(C)C>[OH:27][C@@H:23]1[CH2:24][CH2:25][CH2:26][C@H:22]1[NH:21][C:2]1[C:3]2[N:4]=[CH:5][N:6]([C:7]=2[N:8]=[C:9]([CH3:11])[N:10]=1)[C@@H:12]1[O:18][C@H:17]([CH2:19][OH:20])[C@@H:15]([OH:16])[C@H:13]1[OH:14]

Participants

4

Reactant 2

HCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-ol2×HCID 542785016-chloro-2-methyl-9-(beta-D-ribofuranosyl)-9H-purine

Product 1

HCID 54218717N-(trans-2-Hydroxycyclopentyl)-2-methyladenosineYield 92.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 6-chloro-2-methyl-9-(β-D-ribofuranosyl)-9H-purine (902 mg), trans-2-aminocyclopentanol (404 mg), DEA (517 mg) and isopropanol (35 ml) was heated under reflux with stirring for 22 h under nitrogen. Additional trans-2-aminocyclopentanol (202 mg) and DEA (259 mg) were added and heating under reflux was maintained for a further 5 h. The cooled mixture was concentrated in vacuo and the residual foam (1.9 g) was purified by column chromatography on silica (Merck 9385, deactivated with triethylamine) eluting with System B (10:1) to give a solid (1.01 g). This was repurified by column chromatography on silica (Merck 9385) eluting with System B (10:1) to give the title compound (0.57 g), m.p. 188°-192°.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureunder reflux
  5. temperaturewas maintained for a further 5 h
  6. concentrationThe cooled mixture was concentrated in vacuo
  7. customthe residual foam (1.9 g) was purified by column chromatography on silica (Merck 9385, deactivated with triethylamine)
  8. washeluting with System B (10:1)

Sources & evidence

ORD record
ord-f4ffe6a88c314405b7c5e9a414d5e39a
Source dataset
uspto-grants-1991_07
Patent number
US05032583

Reaction notes

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