Methyl iodide → Cholesterol

HRID 397236Notes

Reaction equation

[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:36])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:35])[CH2:22][CH2:23][C@H:24]([O:26]C(NCCN(C)C)=O)[CH2:25][C:20]4=[CH:19][CH2:18][C@H:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7].Cl.IC>>[CH3:8][CH:6]([CH2:5][CH2:4][CH2:3][C@H:2]([C@@H:9]1[C@:13]2([CH3:36])[C@H:12]([C@H:17]3[C@H:16]([CH2:15][CH2:14]2)[C@:21]2([CH3:35])[C:20]([CH2:25][C@H:24]([CH2:23][CH2:22]2)[OH:26])=[CH:19][CH2:18]3)[CH2:11][CH2:10]1)[CH3:1])[CH3:7]

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 16219102DC-cholesterol hydrochloride

Product 1

HCID 5997Cholesterol

Procedure

3-β-[N(N′,N′,N′-trimethylethane)carbamoyl]cholesterol (TC-Chol), a quaternary ammonium derivative of Chol, was synthesized by methylation of DC-Chol with iodomethane.

Sources & evidence

ORD record: ord-6710d937e459414291f1e8276b7a03df
Source dataset: uspto-grants-2003_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06610321B2

Reaction notes

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