Potassium Carbonate → HCID 89783639, compound

HRID 1056130Notes

Reaction equation

HRID 1056130 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@@H:11]1[C:15]2[N:16](S(C3C=CC(C)=CC=3)(=O)=O)[CH:17]=[CH:18][C:14]=2[C:13](=[O:29])[NH:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CO>[CH2:1]([O:8][CH2:9][CH2:10][C@@H:11]1[C:15]2[NH:16][CH:17]=[CH:18][C:14]=2[C:13](=[O:29])[NH:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 118512009HCID 118512009, compound

Product 1

HCID 89783639HCID 89783639, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-6-(2-(benzyloxy)ethyl)-1-tosyl-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (724e, 3.51 g, 8.55 mmol) in MeOH (50 mL) in an ice bath was added K2CO3 (2.36 g, 17.10 mmol) in one portion. The resulting white suspension was stirred in an ice bath for 1 h and at RT for 1 h. The resulting suspension was filtered through a pad of Celite washing with MeOH. 10 g silica gel was added to the filtrate and concentrated in vacuo. The resulting solid was purified using an ISCO Combiflash RF (40 g Grace Reverlis column, using a gradient of 0-10% 2 M NH3/MeOH in DCM) affording (R)-6-(2-(benzyloxy)ethyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (724f; 1.84 g, 7.17 mmol, 84% yield) as an orange-brown viscous oil. m/z (ESI, +ve) 257.1 (M+1)+. The material (724f) was further purified by chiral SFC (mobile phase CO2/30% MeOH (20 mM NH3), chiral column AS (250×30 mm), wave length 245 nm, flow rate 120 mL/min) The first eluting peak was collected and concentrated in vacuo to give (S)-6-(2-(benzyloxy)ethyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (724g) (537 mg, 3.04 mmol, 24% yield, >99% ee) as an orange tar. The second eluting peak was collected and concentrated in vacuo to give (R)-6-(2-(benzyloxy)ethyl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (724) (780 mg, 3.04 mmol, 35% yield, >99% ee) as an orange tar. 1H NMR (400 MHz, CDCl3) δ ppm 8.46 (1H, br. s.), 7.33-7.44 (5H, m), 6.58 (1H, t, J=2.3 Hz), 6.32 (1H, dd, J=2.8, 1.9 Hz), 5.70 (1H, br. s.), 4.56 (2H, s), 4.52 (1H, dd, J=8.4, 4.7 Hz), 3.77 (2H, dd, J=6.7, 4.3 Hz), 1.90-2.07 (2H, m). m/z (ESI, +ve) 257.1 (M+1)+.

Workup

  1. filtrationThe resulting 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. customThe resulting solid was purified

Sources & evidence

ORD record
ord-fe5c54bbe0e24b09ae80004a1cda0e09
Source dataset
uspto-grants-2016_07
Patent number
US09394297B2

Reaction notes

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