Ammonia → HCID 58426084, compound

HRID 2421815Notes

Reaction equation

HRID 2421815 reaction equation
[F:1][C:2]1([F:13])[CH:10]([F:11])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.[NH3:14].[BH4-].[Na+].Cl.[OH-].[Na+]>CCO.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].CCOCC>[NH2:14][CH:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]([F:11])[C:2]1([F:13])[F:1]

Participants

9

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydrideHCID 58426076HCID 58426076, compound

Product 1

HCID 58426084HCID 58426084, compound

Reagents, catalysts & solvents 3

HCID 11026Titanium isopropoxideCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2,2,3-trifluoro-indanone (282 mg, 1.5 mmol), titanium isopropoxide (0.886 ml, 2.99 mmol) and ammonia (2M in EtOH, 2.5 ml) in EtOH was stirred for 5 hours. The mixture was cooled to 0° C. and NaBH4 (85 mg, 2.25 mmol) added. After stirring for 2 hours the mixture was left at room temperature overnight, then poured onto NH4OH (25%, 10 ml) and extracted with EtOAc. The organic phase was washed with water, dried, and evaporated to yield the crude product (205 mg) as a brown oil. This was shaken between ether and HCl (2M aq.), basified with NaOH (2M) and extracted into ether. Evaporation yielded 1-amino-2,2,3-trifluoro-indane (90 mg) as an oil.

Workup

  1. waitwas left at room temperature overnight
  2. additionpoured onto NH4OH (25%, 10 ml)
  3. extractionextracted with EtOAc
  4. washThe organic phase was washed with water
  5. customdried
  6. customevaporated
  7. customto yield the crude product (205 mg) as a brown oil
  8. extractionextracted into ether
  9. customEvaporation

Sources & evidence

ORD record
ord-5c56f9ef4c39462fb18f890d25e3de02
Source dataset
uspto-grants-2011_06
Patent number
US07960310B2

Reaction notes

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