2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → HCID 67237961, compound

HRID 1985722Notes

Reaction equation

HRID 1985722 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](Br)=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[Si:28]([O:35][CH2:36][CH:37]=[O:38])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>C1(C)C=CC=CC=1.CCCCC>[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:37]([OH:38])[CH2:36][O:35][Si:28]([C:31]([CH3:33])([CH3:32])[CH3:34])([CH3:29])[CH3:30])=[CH:14][CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 86590113(4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl esterHCID 178418306HCID 178418306, compound

Product 1

HCID 67237961HCID 67237961, compoundYield 46.5%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8003PentaneSolvent

Procedure

To a solution of 4.00 g (4R,9aR)-6-bromo-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 100 ml toluene was added drop wise at −78° C. 10.86 ml of a 1.5M solution of tert-butyllithium in pentane. The mixture was stirred at this temperature for 30 min. To the resulting solution was added 5.017 g (tert-butyldimethylsilyloxy) acetaldehyde and the mixture was stirred at −78° C. for 30 min. The reaction was quenched by addition of 10% aqueous ammonium chloride. The phases were separated and the organic phase was purified by chromatography on silica gel with heptane:ethyl acetate=4:1 to yield 2.34 g (4R,9aR)-6-[2-(tert-butyl-dimethyl-silanyloxy)-1-hydroxy-ethyl]-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester as slightly yellow oil (MS: 464.4 (M+H+))

Workup

  1. stirringthe mixture was stirred at −78° C. for 30 min
  2. customThe reaction was quenched by addition of 10% aqueous ammonium chloride
  3. customThe phases were separated
  4. customthe organic phase was purified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-36e4f3aaba0649499fd9ce9a85c576a3
Source dataset
uspto-grants-2009_06
Patent number
US07547699B2

Reaction notes

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