N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5-Dimethylaminomethylene-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester

HRID 481078Notes

Reaction equation

HRID 481078 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][C:8]=2[N:9](C(OC(C)(C)C)=O)[CH:10]=1)=[O:5])[CH3:2].[CH3:24][N:25]([CH:27](N(C)C)N(C)C)[CH3:26]>CCOCC>[CH2:1]([O:3][C:4]([C:6]1[C:7]2[C:22](=[O:23])[C:21](=[CH:24][N:25]([CH3:27])[CH3:26])[CH2:20][CH2:19][CH2:18][C:8]=2[NH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 206056554-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

Product 1

HCID 590720525-Dimethylaminomethylene-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl esterYield 87.1%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 4-oxo-5,6,7,8-tetrahydro-4H-cyclohepta[b]pyrrole-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (1.13 g, 3.52 mmol) and tris(dimethylamino)methane (1.02 g, 7.04 mmol) is stirred at 60° C. in a sealed tube for 4.5 h. After cooling, the thick slurry is taken up in Et2O and filtered. The solid is washed with Et2O and dried, affording 847 mg (87%) of 5-dimethylaminomethylene-4-oxo-1,4,5,6,7,8-hexahydro-cyclohepta[b]pyrrole-3-carboxylic acid ethyl ester as a light yellow-orange solid. 1H NMR (CDCl3, 300 MHz) δ9.93 (br s, 1H), 7.58 (s, 1H), 7.12 (d, J=2.7 Hz, 1H), 4.21 (q, J=7.2 Hz, 2H), 3.06 (s, 6H), 2.68 (m, 2H), 2.47 (m, 2H), 1.80 (m, 2H), 1.26 (t, J=7.2 Hz, 3H).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltered
  3. washThe solid is washed with Et2O
  4. customdried

Sources & evidence

ORD record
ord-c6c5461c1d2343b896f5bc347c04ee57
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

Loading…