Lithium borohydride → HCID 69357319, compound

HRID 1272172Notes

Reaction equation

HRID 1272172 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]([CH:22]=[O:23])=[C:14]([F:24])[CH:13]=3)[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][C:15]([CH2:22][OH:23])=[C:14]([F:24])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86596366HCID 86596366, compound

Product 1

HCID 69357319HCID 69357319, compoundYield 80.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.58 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 in 10 mL tetrahydrofuran was added 0.038 g lithium borohydride and the mixture was stirred at room temperature for 30 min. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was evaporated to dryness and purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 0.468 g (4R,9aR)-7-fluoro-6-hydroxymethyl-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester as yellowish crystals; m.p.: 91–93° C.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. customThe phases were separated
  3. customthe organic phase was evaporated to dryness
  4. custompurified by chromatography on silica gel with heptane

Sources & evidence

ORD record
ord-5e81fd8c71f8407791e2d7201b3ddec1
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

Loading…