Methyl iodide → HCID 86745972, compound

HRID 864751Notes

Reaction equation

[CH2:1]([N:8]1[C:18](=[O:19])[CH:17]2[CH:12]([CH2:13][C:14](=[O:23])[CH2:15][CH:16]2[CH:20]([CH3:22])[CH3:21])[S:9]1(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].[CH3:26]I.[H-].[Na+]>>[CH2:1]([N:8]1[C:18](=[O:19])[CH:17]2[C:12](=[CH:13][CH:14]([O:23][CH3:26])[CH2:15][CH:16]2[CH:20]([CH3:21])[CH3:22])[S:9]1(=[O:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 4311764Sodium borohydride

HCID 86745973HCID 86745973, compound

Product 1

HCID 86745972HCID 86745972, compound

Procedure

2-Benzyl-4-isopropyl-6-oxo-tetrahydrosaccharin of preparation 21 is reduced with sodium borohydride and methylated with methyl iodide in the presence of sodium hydride to provide 2-benzyl-4-isopropyl-6-methoxy-tetrahydrosaccharin. This is debenzylated and chloromethylated as in preparation 21 to provide 2-chloromethyl-4-isopropyl-6-methoxy-4,5,6,7-tetrahydrosaccharin.

Sources & evidence

ORD record: ord-b26fe7242d2e4bbf962b06f697729d95
Source dataset: uspto-grants-1996_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05563163

Reaction notes

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