HCID 117966280, compound → HCID 117966443, compound

HRID 931098Notes

Reaction equation

HRID 931098 reaction equation
[CH2:1]1[N:5]=[C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[N:3]2[CH2:19][CH2:20][CH2:21][CH:2]12>C1(C)C=CC=CC=1>[CH:1]1[N:5]=[C:4]([CH:6]2[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:7]2)[N:3]2[CH2:19][CH2:20][CH2:21][C:2]=12

Participants

3

Reactant 1

HCID 117966280HCID 117966280, compound

Product 1

HCID 117966443HCID 117966443, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
115 °C

Procedure

To a solution of tert-butyl 3-(5,6,7,7a-tetrahydro-1H-pyrrolo[1,2-c]imidazol-3-yl)piperidine-1-carboxylate (175 mg, 0.6 mmol) in toluene (5 mL) was added BaMnO4 (2.1 g, 18 mmol) and the reaction was heated at 115° C. for 42 h. The reaction was cooled to room temperature and BaMnO4 (2 g) was added followed by toluene (2 mL). The reaction mixture was heated to 115° C. for 3 days. The mixture was cooled to room temperature and filtered through Celite followed by rinsing with dichloromethane. The filtrate was concentrated under reduced pressure and the residue was purified via HPLC to afford tert-butyl 3-(6,7-dihydro-5H-pyrrolo[1,2-c]imidazol-3-yl)piperidine-1-carboxylate as an oil (25 mg, 14%). MS (ES+) (M+H) 292.2; LCMS retention time: 1.69 minutes (Method M).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. temperatureThe reaction mixture was heated to 115° C. for 3 days
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through Celite
  5. washby rinsing with dichloromethane
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customthe residue was purified via HPLC

Sources & evidence

ORD record
ord-7990401f3b1a418cae8ba944866afb0a
Source dataset
uspto-grants-2016_03
Patent number
US09296745B2

Reaction notes

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