Trifluoroacetic anhydride → Lilolidine

HRID 1894730Notes

Reaction equation

HRID 1894730 reaction equation
[CH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH:2]=1.C([BH3-])#N.[Na+].FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[K+]>CO.O>[CH2:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[CH2:2]1

Participants

7

Reactant 4

HCID 9845Trifluoroacetic anhydrideHCID 14797Potassium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 156456291-Azatricyclo[6.3.1.0,4,12]dodeca-2,4,6,8(12)-tetraene

Product 1

HCID 120264LilolidineYield 98.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline (4.0 g, 25.5 mmol) in methanol (100 ml) was treated with sodium cyanoborohydride (1.5 g, 23.9 mmol) then cooled to 0° C. Trifluoroacetic anhydride (15 ml) was added dropwise over 15 minutes, then the reaction was allowed to warm to room temperature and stirred for a further 2 hours. The reaction was basified with 5M aqueous potassium hydroxide then diluted with water (500 ml). The mixture was extracted with dichloromethane (3×100 ml) and the combined organic extracts were dried with anhydrous sodium sulfate and evaporated to dryness to obtain 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinoline as a colorless oil (4.0 g) which was used without further purification. LCMS: 160 [M+H].

Workup

  1. temperatureto warm to room temperature
  2. extractionThe mixture was extracted with dichloromethane (3×100 ml)
  3. dry with materialthe combined organic extracts were dried with anhydrous sodium sulfate
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-d02f17d1a1ac4afbb9529876aead0dbe
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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