Lithium Hydroxide → HCID 58576160, compound

HRID 511167Notes

Reaction equation

HRID 511167 reaction equation
C[O:2][C:3](=[O:6])[CH:4]=[CH2:5].C(N(CC)CC)C.[C:14]([C:18]1[CH:23]=[CH:22][C:21]([N:24]2[CH2:31][CH:30]3[CH:26]([CH2:27][NH:28][CH2:29]3)[CH2:25]2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].[OH-].[Li+:33]>O.C(#N)C.O1CCCC1>[Li+:33].[C:14]([C:18]1[CH:19]=[CH:20][C:21]([N:24]2[CH2:31][CH:30]3[CH2:29][N:28]([CH2:5][CH2:4][C:3]([O-:2])=[O:6])[CH2:27][CH:26]3[CH2:25]2)=[CH:22][CH:23]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

8

Reactant 4

HCID 3939Lithium HydroxideHCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 58576432HCID 58576432, compound

Product 1

HCID 58576160HCID 58576160, compoundYield 72.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Acrylic acid methyl ester (189 mg; 2.20 mmol) and triethylamin (0.2 mL) are added to 2-(4-tert-butyl-phenyl)-octahydro-pyrrolo[3,4-c]pyrrole (450 mg; 1.84 mmol) in a 1 to 1 mixture of water and tetrahydrofuran (1.6 mL) and the resulting mixture is irradiated in a mono-mode microwave oven for 30 minutes at 120° C. Lithium hydroxide (92 mg; 3.84 mmol) in water (5 mL) is then added and the reaction mixture is again irradiated in a mono-mode microwave oven for 30 minutes at 100° C. The mixture is then diluted with acetonitrile and the precipitate formed is filtered, collected and dried under high vacuum to afford the desired product (425 mg; 1.34 mmol).

Workup

  1. customthe resulting mixture is irradiated in a mono-mode microwave oven for 30 minutes at 120° C
  2. customthe reaction mixture is again irradiated in a mono-mode microwave oven for 30 minutes at 100° C
  3. customthe precipitate formed
  4. filtrationis filtered
  5. customcollected
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-563d830847dd457a846d353e506e344c
Source dataset
uspto-grants-2015_08
Patent number
US09096524B2

Reaction notes

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