Lithium borohydride → HCID 11667216, compound

HRID 1272183Notes

Reaction equation

HRID 1272183 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])[C:13]=3[CH:23]=[O:24])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[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])[C:13]=3[CH2:23][OH:24])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 87797502HCID 87797502, compound2×

Product 1

HCID 11667216HCID 11667216, compoundYield 69.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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 (intermediate i, examples 54–61) in 15 mL tetrahydrofurane was added 0.052 g lithium borohydride and the mixture was stirred at room temperature for 0.5 h. The reaction mixture was partitioned between water and ethyl acetate. The organic phase was washed twice with water dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel with methylenechloride:ethyl acetate (3:2) to yield 0.56 g (4R,9aR)-7-fluoro-8-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester as colorless foam.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washThe organic phase was washed twice with water
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel with methylenechloride:ethyl acetate (3:2)

Sources & evidence

ORD record
ord-af5f156be23645049fed9a54015e280b
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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