Ammonium Hydroxide → (+/-)-(1R,2S,3R,5S)-3-(6-Amino-9H-purin-9-yl)-5-(chloromethyl)-1,2-cyclopentanediol

HRID 2248362Notes

Reaction equation

[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[CH2:15][C@H:14]([CH2:16]O)[C@@H:13]([OH:18])[C@H:12]1[OH:19].S(Cl)([Cl:22])=O.[OH-].[NH4+]>CN(C)P(N(C)C)(N(C)C)=O>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[CH2:15][C@H:14]([CH2:16][Cl:22])[C@@H:13]([OH:18])[C@H:12]1[OH:19]

Participants

Conditions

Temperature: 25 °C

Procedure

(±)-(1R*,2S*,3R*,5R*)-3-(6-Amino-9H-purin-9-yl)-5-(hydroxymethyl)-1,2-cyclopentanediol (J. Am. Chem. Soc. 1969, 91, 3075) (0.94 g, 3.54 mmol) was stirred in hexamethylphosphoramide (13 ml) with cooling (ice bath) while thionyl chloride was added. The mixture was stirred under nitrogen at 25° C. for 18 hours. Ice water (50 ml) was added to the cooled mixture. The resulting solution was neutralized with concentrated ammonium hydroxide. The white precepitate was filtered off and dissolved in refluxing methanol (125 ml). Concentrated ammonium hydroxide (10 ml) was added and the solution allowed to cool slowly to 25° C. over 1 hour. The methanol was evaporated and the residual solid slurried in cold water and filtered to give title compound as an off-white powder (0.92 g, 92%); mp 188°-189° C. dec.

Workup

additionwas added
filtrationThe white precepitate was filtered off
dissolutiondissolved
temperaturein refluxing methanol (125 ml)
additionConcentrated ammonium hydroxide (10 ml) was added
temperatureto cool slowly to 25° C. over 1 hour
customThe methanol was evaporated
filtrationthe residual solid slurried in cold water and filtered

Sources & evidence

ORD record: ord-75808a2ea6654a29b6548c5f4a92ec02
Source dataset: uspto-grants-1991_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05039689

Reaction notes

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