3-Methyl-2-butanone → (4R,9aR)-6-(1-(RS)-Hydroxy-1,2-dimethyl-propyl)-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester

HRID 11953

Reaction equation

HRID 11953 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]([CH2:22][O:23]CCO)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:27]([Li])[CH2:28][CH2:29]C.[CH3:32]C(C)C(=O)C>>[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:22]([OH:23])([CH3:32])[CH:28]([CH3:29])[CH3:27])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

4

Reactant 3

HCID 112513-Methyl-2-butanoneHCID 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 69556836(4R,9aR)-6-(1-(RS)-Hydroxy-1,2-dimethyl-propyl)-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 3-methyl-2-butanone.

Sources & evidence

ORD record
ord-1b6e5e145c19478197b39aa10504cac1
Source dataset
uspto-grants-2006_08
Patent number
US07098337B2

Linked notes

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