tert-Butoxy bis(dimethylamino)methane → HCID 89631940, compound

HRID 1502571Notes

Reaction equation

HRID 1502571 reaction equation
[CH2:1]([C:4]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:5]=1[CH2:6][CH:7]1[CH2:11][C:10](=[O:12])[N:9]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH:8]12)[CH:2]=[CH2:3].C(O[CH:29](N(C)C)[N:30]([CH3:32])[CH3:31])(C)(C)C>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:1]([C:4]1[CH:23]=[CH:22][CH:21]=[C:20]2[C:5]=1[CH2:6][CH:7]1[CH:8]2[N:9]([C:13]([O:15][C:16]([CH3:18])([CH3:19])[CH3:17])=[O:14])[C:10](=[O:12])/[C:11]/1=[CH:29]\[N:30]([CH3:32])[CH3:31])[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 79885tert-Butoxy bis(dimethylamino)methaneHCID 89618125HCID 89618125, compound

Product 1

HCID 89631940HCID 89631940, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the tert-butyl 5-allyl-2-oxo-3,3a,4,8b-tetrahydroindeno[1,2-b]pyrrole-1-carboxylate (Step 4, 0.21 g, 0.7 mmol) in tert-butoxybis(dimethylamino)methane (0.415 mL, 2.0 mmol) in toluene (3 ml) was heated at 110° C. overnight. The solution was diluted with ethyl acetate and washed twice with water, brine, dried over magnesium sulphate and concentrated to give tert-butyl (3Z)-5-allyl-3-(dimethylaminomethylene)-2-oxo-4,8b-dihydro-3aH-indeno[1,2-b]pyrrole-1-carboxylate D1 (colourless solid, 0.24 g, 97%). This compound was used without extra purification. LC-MS (Method C) RT 1.05 min, 369 (M+H+). This method was used to prepare compound D2 to D13 (table D).

Workup

  1. washwashed twice with water, brine
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a6989bd35f4d469bb4f375273453173f
Source dataset
uspto-grants-2015_12
Patent number
US09210929B2

Reaction notes

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