N,N,N',N'-Tetramethylethylenediamine → 1-(1,1-Dimethylethyl) 7-ethyl 2,3-dihydro-1H-indole-1,7-dicarboxylate

HRID 656001Notes

Reaction equation

HRID 656001 reaction equation
C([Li])(CC)C.[N:6]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7]1.CN(C)CCN(C)C.Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32]>C(OCC)C.O>[N:6]1([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:31]([O:33][CH2:34][CH3:35])=[O:32])[CH2:8][CH2:7]1

Participants

7

Reactant 4

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10928Ethyl chloroformateHCID 3663954tert-Butyl indoline-1-carboxylateHCID 178418400CID 53628100

Product 1

HCID 593325671-(1,1-Dimethylethyl) 7-ethyl 2,3-dihydro-1H-indole-1,7-dicarboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

A 1.3 M solution of sec-butyl lithium in cyclohexanes (1642 mL, 2.13 mol) was added dropwise to a solution of 1,1-dimethylethyl 2,3-dihydro-1H-indole-1-carboxylate (300 g, 1.37 mol) and N,N,N′,N′ tetramethyl-1,2-ethanediamine (248 mL, 1.64 mol) in dry diethyl ether (2.5 L) at −78° C. The reaction mixture was stirred for 2 hours at this temperature and ethyl chloroformate (143.9 mL, 1.50 mol) was added dropwise to the mixture at −78° C. After the addition, the reaction was allowed to warm to room temperature overnight. Water (1 L) was added carefully to the mixture and the organic layer was separated and dried (Na2SO4). The solution was concentrated and the residue was purified by silica-gel column chromatography (PE:EA=10:1), giving 150 g (38%) of the title compound.

Workup

  1. additionwas added dropwise to the mixture at −78° C
  2. additionAfter the addition
  3. customthe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationThe solution was concentrated
  6. customthe residue was purified by silica-gel column chromatography (PE:EA=10:1)

Sources & evidence

ORD record
ord-95efa3171ff34ad4a4215187f0aeb9c9
Source dataset
uspto-grants-2011_12
Patent number
US08071584B2

Reaction notes

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