Methyl iodide → HCID 101062134, compound

HRID 1452787Notes

Reaction equation

HRID 1452787 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. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 30 min
  3. custom10-Methoxy-ginkgolide B was separated

Sources & evidence

ORD record
ord-5d7d9411ff424289bf595222462f26bd
Source dataset
uspto-grants-2009_01
Patent number
US07473788B2

Reaction notes

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