Hydrochloric Acid → 1-(16-Hydroxyheptadecyl)-3,7-dimethylxanthine

HRID 964554Notes

Reaction equation

[BH4-].[Na+].[OH:3][CH:4]([CH2:33]O)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:29](=[O:30])[C:28]2[N:27]([CH3:31])[CH:26]=[N:25][C:24]=2[N:23]([CH3:32])[C:21]1=[O:22].Cl>C(O)C>[OH:3][CH:4]([CH3:33])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][N:20]1[C:29](=[O:30])[C:28]2[N:27]([CH3:31])[CH:26]=[N:25][C:24]=2[N:23]([CH3:32])[C:21]1=[O:22]

Participants

Conditions

Temperature: 60 °C

Procedure

0.25 g of 1-(16,17-oxidoheptadecyl)-3,7-dimethylxanthine (0.58 mmol) was dissolved in ethanol (5 ml). Sodium borohydride (0.34 g, 0.93 mmol) was added to the ethanol solution and the reaction stirred at 60° C. for 16 hours. Hydrochloric acid (1.0M, 10 ml) was added and extracted with dichloromethane (2×30 ml). The combined extracts were dried over magnesium sulfate. Evaporated solvent left 0.225 g of 1-(16-hydroxyheptadecyl)-3,7-dimethylxanthine as a white solid (90% yield).

Workup

extractionextracted with dichloromethane (2×30 ml)
dry with materialThe combined extracts were dried over magnesium sulfate

Sources & evidence

ORD record: ord-6cb5dc8d75f54a4f85361d37d8102b3d
Source dataset: uspto-grants-1998_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05770595

Reaction notes

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