Methoxyacetone → (4R,9aR)-6-(1-(RS)-Hydroxy-2-methoxy-1-methyl-ethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11954

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15](COCCO)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH3:32][O:33][CH2:34][C:35](=[O:37])[CH3:36]>>[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C@H:10]([CH2:11][C:12]3[C:17]2=[N:16][C:15]([C:35]([OH:37])([CH3:36])[CH2:34][O:33][CH3:32])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 3

HCID 22172Methoxyacetone

HCID 69557393(4R,9aR)-6-(2-hydroxy-ethoxymethyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester2×

HCID 178418339Butyllithium

Product 1

HCID 69555945(4R,9aR)-6-(1-(RS)-Hydroxy-2-methoxy-1-methyl-ethyl)-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 51, intermediate, from (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (Example 5, intermediate b), n-butyllithium and methoxy-2-propanone.

Sources & evidence

ORD record: ord-3aeb048e68654783bf2fca302fc4dc25
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07098337B2

Linked notes

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