Triethylamine → HCID 44343895, compound

HRID 1379635Notes

Reaction equation

HRID 1379635 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[NH2:7].[CH:8]1[N:13]=[C:12](Cl)[C:11]2[N:15]=[CH:16][N:17]([C@@H:18]3[O:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[C@H:19]3[OH:26])[C:10]=2[N:9]=1.C(N(CC)CC)C>O1CCOCC1>[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[NH:7][C:12]1[C:11]2[N:15]=[CH:16][N:17]([C:10]=2[N:9]=[CH:8][N:13]=1)[C@@H:18]1[O:22][C@H:21]([CH2:23][OH:24])[C@@H:20]([OH:25])[C@H:19]1[OH:26]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 930036-Chloropurine ribosideHCID 10464306rac-(1R,2R)-2-aminocyclopentan-1-ol

Product 1

HCID 44343895HCID 44343895, compoundYield 18.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Trans-2-hydroxycyclopentylamine (0.35 g, 3.46 mmol)(prepared by reaction of cyclopentene oxide with ammonia in a sealed vessel: see example 11) was reacted with 6-chloropurine riboside (i.e. 9-β-D-ribofuranosyl-9H-purine) (0.5 g, 1.7 mmol) in dioxan (30 ml) in the presence of triethylamine (0.93 g, 9 mmol). The reaction mixture was heated at 100° C. for 70 h, cooled and evaporated. The resultant residue was purified by flash chromatography eluting with a mixture of ethyl acetate and methanol (19:1). The fractions found to contain the highest amounts of N-[(1R, trans)-2-hydroxycyclopentyl]adenosine following HPLC examination, were combined and evaporated to a solid (0.17 g). Recrystallisation from methanol provided the pure N-[(1R, trans)-2-hydroxycyclopentyl]adenosine (0.11 g, 18%) mp 233°-235° C. 1H NMR (DMSO-d6)δ 1.43-2.12 (6H, 4m, --CH2CH2CH2 --), 3.52-3.59 (1H, m, H-5'a), 3.54-3.71 (1H, m, H-5'b), 3.97 (1H, q, H-4'), 4.07 (1H, br, --C HOH) 4.15 (1H, q, H-3'), 4.61 (1H, q, H-2'), 4.87, 5.21, 5.41-5.47 (4H, d & 3m, OH groups), 5.89 (1H, d, H-1'), 7.75 (1H, br d, --NH), 8.21 and 8.37 (H-2 and H-8).

Workup

  1. temperaturecooled
  2. customevaporated
  3. customThe resultant residue was purified by flash chromatography
  4. washeluting with a mixture of ethyl acetate and methanol (19:1)
  5. customevaporated to a solid (0.17 g)
  6. customRecrystallisation from methanol

Sources & evidence

ORD record
ord-b9d0406d64854439b78969b7d138997a
Source dataset
uspto-grants-1997_09
Patent number
US05672588

Reaction notes

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