Sodium cyanoborohydride → methyl (5-fluoro-2,3-dihydro-1H-indol-3-yl)-acetate

HRID 74512Notes

Reaction equation

HRID 74512 reaction equation
C([BH3-])#N.[Na+].[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[C:9]2[CH2:15][C:16]([O:18][CH3:19])=[O:17]>C(O)(=O)C>[F:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH2:10][CH:9]2[CH2:15][C:16]([O:18][CH3:19])=[O:17]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydride2×HCID 21638377Methyl 5-Fluoroindole-3-acetate

Product 1

HCID 58386643methyl (5-fluoro-2,3-dihydro-1H-indol-3-yl)-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Under a nitrogen atmosphere 910 mg (14.5 mmol) sodium cyanoborohydride was added batchwise to 1.0 g (4.83 mmol) methyl (5-fluoro-1H-indol-3-yl)-acetate in 12.5 g acetic acid while cooling slightly. After 2 h stirring at RT another 910 mg (14.5 mmol) sodium cyanoborohydride was added batchwise while cooling slightly. After 3 h stirring at RT the solvent was evaporated down using the rotary evaporator. The residue was taken up in 4M hydrochloric acid and stirred for 30 min. Then the reaction solution was made alkaline with solid potassium carbonate and extracted with dichloromethane (3×). The combined organic phases were dried on sodium sulphate, filtered and evaporated down using the rotary evaporator. The product thus obtained was reacted directly.

Workup

  1. temperaturewhile cooling slightly
  2. additionwas added batchwise
  3. temperaturewhile cooling slightly
  4. customwas evaporated down
  5. customthe rotary evaporator
  6. stirringstirred for 30 min
  7. extractionextracted with dichloromethane (3×)
  8. customThe combined organic phases were dried on sodium sulphate
  9. filtrationfiltered
  10. customevaporated down
  11. customthe rotary evaporator
  12. customThe product thus obtained
  13. customwas reacted directly

Sources & evidence

ORD record
ord-bdf2fd7fb4c2495fa3dcc8aee490d59e
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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