Sodium cyanoborohydride → HCID 69357759, compound

HRID 1272170Notes

Reaction equation

HRID 1272170 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:20][C@@H:19]([CH3:21])[N:18]2[C:10](=[CH: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([BH3-])#N.[Na+]>C(O)(=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][CH:15]=[C:14]([F:22])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 69358754HCID 69358754, compound

Product 1

HCID 69357759HCID 69357759, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

T a solution of 0.907 g (R)-7-fluoro-4-methyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (0.0030 mol) in 12 mL of glacial acetic acid was added in 2 portions 0.936 g sodium cyanoborohydride (0.015 mol) with cooling. The mixture was then stirred at ambient temperature for 2 h. The solvent was evaporated and the residue was partitioned between water (adjusted to pH 10–11 by addition of aqueous sodium hydroxide solution) and dichloromethane. The organic phase was evaporated to dryness then purified by chromatography on silica gel with heptane:ethyl acetate (2:1) to yield a slightly yellow oil which solidified on standing to yield 0.852g [4R,9aR]-7-fluoro-4-methyl-3,4,9,9a-tetrahydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester (94% th) slightly yellow crystals; m.p.: 56.6–58.4° C.

Workup

  1. temperaturewith cooling
  2. customThe solvent was evaporated
  3. customthe residue was partitioned between water (adjusted to pH 10–11 by addition of aqueous sodium hydroxide solution) and dichloromethane
  4. customThe organic phase was evaporated to dryness
  5. customthen purified by chromatography on silica gel with heptane:ethyl acetate (2:1)
  6. customto yield a slightly yellow oil which

Sources & evidence

ORD record
ord-838d69f9535a49309c70ade3da442655
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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