Methyl iodide → (4R,9aR)-6-(1-(S)-Methoxy-ethyl)-7-methoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 1272159Notes

Reaction equation

Cl[C:2]1N=C2C(=CC=1OCC)C=C1N2C(C)CNC1.[C:19]([O:23][C:24]([N:26]1[CH2:38][C@@H:37]([CH3:39])[N:36]2[C@H:28]([CH2:29][C:30]3[C:35]2=[N:34][C:33]([C@@H:40]([O:42][CH3:43])[CH3:41])=[C:32]([CH2:44][OH:45])[CH:31]=3)[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20].[H-].[Na+].CI>>[C:19]([O:23][C:24]([N:26]1[CH2:38][C@@H:37]([CH3:39])[N:36]2[C@H:28]([CH2:29][C:30]3[C:35]2=[N:34][C:33]([C@@H:40]([O:42][CH3:43])[CH3:41])=[C:32]([CH2:44][O:45][CH3:2])[CH:31]=3)[CH2:27]1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

Reactant 4

HCID 6328Methyl iodide

HCID 24758Sodium hydride

HCID 184559876-Chloro-7-ethoxy-4-methyl-1,2,3,4-tetrahydro-2,4a,5-triaza-fluorene

HCID 69360238(4R,9aR)-7-hydroxymethyl-6-(1-(S)-methoxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Product 1

HCID 69359519(4R,9aR)-6-(1-(S)-Methoxy-ethyl)-7-methoxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

Procedure

This compound was prepared in analogy to example 1, intermediate d) from (4R,9aR)-7-hydroxymethyl-6-(1-(S)-methoxy-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester, sodium hydride and methyl iodide.

Sources & evidence

ORD record: ord-694693f6340a4c519d6fa921943bc887
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208494B2

Reaction notes

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