Benzoyl chloride → HCID 71282812, compound

HRID 1182687Notes

Reaction equation

HRID 1182687 reaction equation
[CH3:1]CN(CC)CC.[CH2:8]1[CH:12]2[CH2:13][NH:14][CH2:15][CH:11]2[CH2:10][N:9]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>C1COCC1>[C:23]([N:14]1[CH2:15][CH2:11][C:12]2([CH2:8][N:9]([C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[CH2:10][CH2:1]2)[CH2:13]1)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 4142526Tert-butyl octahydropyrrolo(3,4-c)pyrrole-2-carboxylate

Product 1

HCID 71282812HCID 71282812, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
115 °C

Procedure

Et3N (0.5 mL) was added into a solution of tert-butyl hexahydropyrrolo[3,4-c]pyrrole-2(1H)-carboxylate (0.2 g) and benzoyl chloride (0.1 mL) in THF (10 mL). The mixture was heated to 115° C. for 24 hours. The reaction was quenched with water (10 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic phase was dried over MgSO4 and concentrated to give a residue which was purified by silica gel chromatography to give tert-butyl 7-benzoyl-2,7-diazaspiro[4.4]nonane-2-carboxylate.

Workup

  1. customThe reaction was quenched with water (10 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customto give a residue which
  6. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-846643860ba44fb9b03aab34c35e7fd8
Source dataset
uspto-grants-2014_03
Patent number
US08664213B2

Reaction notes

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