Potassium Carbonate → HCID 89793832, compound

HRID 1056405Notes

Reaction equation

HRID 1056405 reaction equation
[CH2:1]([C@@H:3]1[C:7]2[N:8](S(C3C=CC(C)=CC=3)(=O)=O)[CH:9]=[CH:10][C:6]=2[C:5](=[O:21])[NH:4]1)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[CH2:1]([C@@H:3]1[C:7]2[NH:8][CH:9]=[CH:10][C:6]=2[C:5](=[O:21])[NH:4]1)[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 89793962HCID 89793962, compound

Product 1

HCID 89793832HCID 89793832, compoundYield 56.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-6-ethyl-1-tosyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (505e, 3.49 g, 11.47 mmol) in MeOH (50 mL) in an ice bath was added potassium carbonate (3.17 g, 22.93 mmol) in one portion. The resulting white suspension was stirred in an ice bath for 1 h and at RT for 1 h. The suspension was filtered through a pad of Celite washing with MeOH. 10 g silica gel was added to the filtrate and concentrated in vacuo. It was purified on the ISCO Combiflash RF (40 g Grace Reveleris column, using a gradient of 0-20% 2 M NH3/MeOH in DCM) affording (R)-6-ethyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (966 mg, 6.43 mmol, 56% yield) as a tan solid. m/z (ESI, +ve) 151.1 (M+1)+. The material was further purified by chiral SFC (mobile phase CO2/15% MeOH (20 mM NH3), chiral column AS (250×30 mm), wave length 245 nm, flow rate 120 mL/min) The second eluting peak was collected and concentrated in vacuo to give (R)-6-ethyl-5,6-dihydropyrrolo[3,4-b]pyrrolo-4(1H)-one (505f, 450 mg, 3.00 mmol, 26% yield) as an off-white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.31 (1H, br. s.), 7.55 (1H, s), 6.83 (1H, t, J=2.3 Hz), 6.07 (1H, dd, J=2.7, 1.6 Hz), 4.31 (1H, t, J=5.9 Hz), 1.50-1.74 (2H, m), 0.85 (3H, t, J=7.4 Hz). m/z (ESI, +ve) 151.1 (M+1)+.

Workup

  1. filtrationThe suspension was filtered through a pad of Celite
  2. washwashing with MeOH
  3. addition10 g silica gel was added to the filtrate
  4. concentrationconcentrated in vacuo
  5. customIt was purified on the ISCO Combiflash RF (40 g Grace Reveleris column

Sources & evidence

ORD record
ord-748e4ec256a4457389467d9b3743ee42
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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