(3aR,6aR)-5-methyl-1-(4'-(1-trityl-1H-pyrazol-4-yl)biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole → (3aR,6aR)-1-(4'-(1H-pyrazol-4-yl)biphenyl-4-yl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

HRID 1947413Notes

Reaction equation

HRID 1947413 reaction equation
[CH3:1][N:2]1[CH2:9][C@@H:8]2[C@@H:4]([N:5]([C:10]3[CH:15]=[CH:14][C:13]([C:16]4[CH:21]=[CH:20][C:19]([C:22]5[CH:23]=[N:24][N:25](C(C6C=CC=CC=6)(C6C=CC=CC=6)C6C=CC=CC=6)[CH:26]=5)=[CH:18][CH:17]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:7]2)[CH2:3]1>C(O)=O>[NH:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:13]3[CH:12]=[CH:11][C:10]([N:5]4[CH2:6][CH2:7][C@@H:8]5[CH2:9][N:2]([CH3:1])[CH2:3][C@H:4]45)=[CH:15][CH:14]=3)=[CH:17][CH:18]=2)[CH:26]=[N:25]1

Participants

3

Reactant 1

HCID 68495764(3aR,6aR)-5-methyl-1-(4'-(1-trityl-1H-pyrazol-4-yl)biphenyl-4-yl)octahydropyrrolo[3,4-b]pyrrole

Product 1

HCID 24743848(3aR,6aR)-1-(4'-(1H-pyrazol-4-yl)biphenyl-4-yl)-5-methyloctahydropyrrolo[3,4-b]pyrrole

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

The product of Example 81A (44 mg, 0.075 mmole) was stirred with 3 ml of formic acid for 4 hours. The mixture was concentrated to dryness and the residue was dissolved in 10% methanol in dichloromethane and stirred with saturated sodium bicarbonate. Two layers were separated and the aqueous layer was extracted with dichloromethane (2×). The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography to provide the title compound. 1H NMR (300 MHz, CDCl3) δ ppm 7.88 (s, 2H) 7.47-7.64 (m, 6H) 6.65 (d, J=8.81 Hz, 2H) 4.11-4.25 (m, 1H) 3.50-3.66 (m, 1H) 3.25-3.37 (m, 1H) 2.92-3.07 (m, 1H) 2.71-2.82 (m, 1H) 2.51-2.69 (m, 3H) 2.34 (s, 3H) 2.13-2.25 (m, 1H) 1.90-2.05 (m, 1H). MS: (M+H)+=345.

Workup

  1. concentrationThe mixture was concentrated to dryness
  2. dissolutionthe residue was dissolved in 10% methanol in dichloromethane
  3. customTwo layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×)
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-a277d45e82324be189310556faaaa911
Source dataset
uspto-grants-2013_03
Patent number
US08399468B2

Reaction notes

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