HCID 67975594, compound → HCID 67975561, compound

HRID 1844095Notes

Reaction equation

HRID 1844095 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])[CH2:11][CH:10]2[CH2:14][C:15]3[C:20]([CH:9]12)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(OC(N(C)C)N(C)C)(C)(C)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[C:12](=[O:13])/[C:11](=[CH:6]\[N:8]([CH3:12])[CH3:9])/[CH:10]2[CH2:14][C:15]3[C:20]([CH:9]12)=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 67975594HCID 67975594, compound

Product 1

HCID 67975561HCID 67975561, compoundYield 197.5%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 79885tert-Butoxy bis(dimethylamino)methaneSolvent

Procedure

A solution of the 2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester F1 (160 mg, 0.586 mmol) in tert-butoxybis(dimethylamino)methane was heated at 75° C. for 4 h. The solution was diluted with ethyl acetate and washed with water, brine, dried and concentrated to give 3-[1-dimethylamino-meth-(Z)-ylidene]-2-oxo-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]pyrrole-1-carboxylic acid tert-butyl ester E1 (colourless solid, 190 mg, 98%). C19H24N2O3; MW: 328.41; LCMS (method A) RT 1.78 min; ES: 329 (MH+), 273; 1H NMR (400 MHz, CDCl3) δ 7.74 (1H, d), 7.15-7.26 (4H, m), 5.61 (1H, d), 3.99 (1H, td), 3.37 (1H, dd), 3.10 (6H, s), 3.06 (1H, dd), 1.60 (9H, s) ppm.

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-eb49ec4f40d8493fa184b355896f3830
Source dataset
uspto-grants-2015_02
Patent number
US08946280B2

Reaction notes

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