Sodium cyanoborohydride → HCID 86596346, compound

HRID 1272112Notes

Reaction equation

HRID 1272112 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][C:15]([Cl:22])=[C:14]([CH3:23])[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][C:15]([Cl:22])=[C:14]([CH3:23])[CH:13]=3)[CH2:9]1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 86596351HCID 86596351, compound

Product 1

HCID 86596346HCID 86596346, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 0.26 g (0.77 mmol) (R)-6-chloro-4,7-dimethyl-3,4-dihydro-1H-2,4a,5-triaza-fluorene-2-carboxylic acid tert-butyl ester in 5 mL acetic acid was added 0.24 g (3.87 mmol) sodium cyanoborohydride. After 2 h the volatile components were removed at a rotary evaporator and the residue was taken up in ethyl acetate and treated with 32% aqueous sodium hydroxide solution until a pH of 11 was obtained. The aqueous phase was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:7) as eluant to give the product as a colourless oil (80.3%).

Workup

  1. customAfter 2 h the volatile components were removed at a rotary evaporator
  2. additiontreated with 32% aqueous sodium hydroxide solution until a pH of 11
  3. customwas obtained
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. washthe combined organic layers were washed with brine
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by column chromatography over silica gel (0.030–0.063 mm) with ethyl acetate:n-hexane (1:7) as eluant

Sources & evidence

ORD record
ord-fdd32195c1b041e2bae4a73224cb53ca
Source dataset
uspto-grants-2007_04
Patent number
US07208494B2

Reaction notes

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