Citric Acid → HCID 86596366, compound

HRID 1272171Notes

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][CH:15]=[C:14]([F:22])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CN(C)[CH:30]=[O:31].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1(C)C=CC=CC=1.C1CCCCC1.O>[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]([CH:30]=[O:31])=[C:14]([F:22])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2.885 g (4R,9aR)-7-fluoro-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 60 mL toluene at −78° C. was added 8.72 mL of a ca. 1.3 M solution of sec. butyl lithium in cyclohexane over 10 min. The orange mixture was stirred at −78° C. for 30 min. To the resulting viscous solution was added 1.00 mL dimethylformamide and the mixture was stirred at −78° C. for 1.5 h. To the reaction mixture was added 100 mL of a 10% citric acid solution in water. The phases were separated and the organic phase was evaporated to dryness and purified by chromatography on silica gel with heptane:ethyl acetate=2:1 to yield 0.585 g (4R,9aR)7-fluoro-6-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester as yellow-orange crystals; m.p.: 139–140° C. and 0.800 g (4R,9aR)-7-Fluoro-8-formyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester.

Workup

stirringthe mixture was stirred at −78° C. for 1.5 h
customThe phases were separated
customthe organic phase was evaporated to dryness
custompurified by chromatography on silica gel with heptane

Sources & evidence

ORD record: ord-a53d709428674034bd733a66deea3fb3
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07208494B2

Reaction notes

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