Methyl iodide → HCID 69413965, compound

HRID 2187284Notes

Reaction equation

HRID 2187284 reaction equation
[Si]([O:8][C@H:9]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@@H:11]([CH2:12][CH2:13][C:14]3[C:15]4[C@:25]([CH3:33])([CH2:26][CH2:27][C:28]=32)[C@@H:18]([C@H:19]([CH3:24])[CH2:20][CH2:21][CH2:22][OH:23])[CH2:17][CH:16]=4)[C:10]1([CH3:35])[CH3:34])(C(C)(C)C)(C)C.[H-].[Na+].[CH3:38]I>CN(C=O)C>[CH3:35][C:10]1([CH3:34])[C@@H:9]([OH:8])[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:11]1[CH2:12][CH2:13][C:14]1[C:15]3[C@:25]([CH3:33])([CH2:26][CH2:27][C:28]=12)[C@@H:18]([C@H:19]([CH3:24])[CH2:20][CH2:21][CH2:22][O:23][CH3:38])[CH2:17][CH:16]=3

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69411676HCID 69411676, compound

Product 1

HCID 69413965HCID 69413965, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3β-tert-Butyldimethylsilyloxy-4,4-dimethyl-5α-chola-8,14-dien-24-ol (100 mg) is methylated with sodium hydride 60% (16 mg) and methyl iodine (0.125 ml) in 1 ml of DMF. The protecting tert-butyldimethylsilyl group is split of by treatment with HCl/ethanol. After aqueous work-up and crystallisation from methanol/water, the title compound (5 mg) is isolated.

Workup

  1. customThe protecting tert-butyldimethylsilyl group is split of by treatment with HCl/ethanol
  2. customAfter aqueous work-up and crystallisation from methanol/water

Sources & evidence

ORD record
ord-0a9ad29cf87c4497a5a887e522c1b2a3
Source dataset
uspto-grants-2002_06
Patent number
US06407086B2

Reaction notes

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