Tert-Butylamine → N-((1S,trans)-2-hydroxycyclopentyl)adenosine

HRID 1086806Notes

Reaction equation

HRID 1086806 reaction equation
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[C:34]2[N:33]=[CH:32][N:31]=[C:23]([NH:24][C@H:25]3[CH2:29][CH2:28][CH2:27][C@@H:26]3[OH:30])[C:22]=2[N:21]=[CH:20]1)(=O)C.C(N)(C)(C)C>CO>[OH:30][C@H:26]1[CH2:27][CH2:28][CH2:29][C@@H:25]1[NH:24][C:23]1[C:22]2[N:21]=[CH:20][N:19]([C:34]=2[N:33]=[CH:32][N:31]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 67639694HCID 67639694, compound

Product 1

HCID 9884817N-((1S,trans)-2-hydroxycyclopentyl)adenosineYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2',3',5'-tri-O-acetyl-N-[(1S,trans)-2-hydroxycyclopentyl]adenosine (0.34 g) in methanol (7 ml) containing t-butylamine (3 ml) was allowed to stand at 23° for 16 h. The solution was evaporated to dryness and residual t-butylamine was removed azeotropically with methanol to leave a glass. Crystallisation of a sample of this glass (0.19 g) from a mixture of methanol and ethyl acetate (1:20) gave the title compound (0.15 g), m.p. 160°-163°. Its chromatographic behaviour resembled that of authentic material.

Workup

  1. customThe solution was evaporated to dryness and residual t-butylamine
  2. customwas removed azeotropically with methanol
  3. customto leave a glass
  4. customCrystallisation of a sample of this glass (0.19 g)
  5. additionfrom a mixture of methanol and ethyl acetate (1:20)

Sources & evidence

ORD record
ord-99c83ddf44eb4562a2066ec93b619fc9
Source dataset
uspto-grants-1991_07
Patent number
US05032583

Reaction notes

Loading…