Methyl iodide → HCID 101062134, compound

HRID 857536Notes

Reaction equation

HRID 857536 reaction equation
[CH3:1][C@H:2]1[C@:7]2([OH:30])[C@:8]34[O:28][C@H:27]5[C@@:16]6([C@@H:23]([OH:29])[C:24]([O:26]5)=[O:25])[C@H:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:18][C@H:12]([C@@:13]36[C@@H:14]([OH:15])[C@@H:6]2[O:5][C:3]1=[O:4])[O:11][C:9]4=[O:10].[C:31]([O-])([O-])=O.[K+].[K+].IC>C(#N)C>[CH3:1][C@H:2]1[C@:7]2([OH:30])[C:8]34[O:28][CH:27]5[C@@:16]6([C@@H:23]([O:29][CH3:31])[C:24]([O:26]5)=[O:25])[C@H:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:18][C@H:12]([C@:13]36[C@H:14]([OH:15])[CH:6]2[O:5][C:3]1=[O:4])[O:11][C:9]4=[O:10]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 6324617HCID 6324617, compound

Product 1

HCID 101062134HCID 101062134, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of ginkgolide B (0.030 g, 0.071 mmol) and K2CO3 (0.030 g, 0.212 mmol) in acetonitrile (0.5 mL) was added iodomethane (0.020 g, 0.141 mmol) The reaction mixture was heated under reflux for 30 min. This reaction resulted in a mixture of 10-methoxy-ginkgolide B and 1-methoxy ginkgolide B in a ratio of 4 to 1. 10-Methoxy-ginkgolide B was separated using an HPLC semi-preparative C18 column (7.8 mm×30 cmL) with a mobile phase of MeOH/H20 (40:60) at a flow of 2 mL/min to give the final product as a white solid (0.017 g, 56%). 1H NMR (400 MHz, CD3OD): δ 1.14 (s, tert-butyl), 1.24 (d, J=7.1, CH3), 1.90 (dd, J=14.2, 4.6, 8-H), 2.06 (td, J=13.9, 4.3, 7α-H), 2.25 (dd, J=13.6, 4.6, 7β-H), 3.05 (q, J=7.1, 14-H), 3.80 (s, OCH3), 4.24 (d, J=7.4, 1-H), 4.57 (d, J=7.4, 2-H), 4.93 (s, 10-H), 5.43 (d, J=4.1, 6-H), 6.10 (s, 12-H). 13C NMR (75 MHz, CD3OD): δ 7.6, 7.0, 29.6 (3 C), 32.9, 37.6, 41.8, 48.8, 68.6, 70.5, 71.5, 74.4, 80.4, 82.2, 84.8, 90.9, 98.2, 110.3, 171.1, 173.0, 175.4. [Hu, L., Chen, Z., Xie, Y., Jiang, Y., & Zhen, H. (2000) Bioorg. Med. Chem. 8, 1515–1521]

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 min
  3. custom10-Methoxy-ginkgolide B was separated

Sources & evidence

ORD record
ord-9ed0736d59df4eb18a4cf3ae6d97b932
Source dataset
uspto-grants-2006_12
Patent number
US07145021B2

Reaction notes

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