4-Methylmorpholine → HCID 23365866, compound

HRID 1080760Notes

Reaction equation

HRID 1080760 reaction equation
Cl[C:2]([O:4][CH:5]1[CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:3].[NH2:10][C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][CH:19]=1)[NH:16][CH:15]=[C:14]2[CH2:20][C:21]1[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=1[O:31][CH3:32].CN1CCOCC1>ClCCl>[CH:5]1([O:4][C:2]([NH:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[C:14]3[CH2:20][C:21]2[CH:30]=[CH:29][C:24]([C:25]([O:27][CH3:28])=[O:26])=[CH:23][C:22]=2[O:31][CH3:32])=[O:3])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 2735892Cyclopentyl chloroformateHCID 23365920Methyl 4-(5-aminoindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365866HCID 23365866, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyclopentyl chloroformate was added to a stirred solution of the amino ester (A) (0.15 g.) and N-methylmorpholine (0.27 g.) in dichloromethane (3 ml.) at 0°-5° C., under an atmosphere of nitrogen. The mixture was stirred for 30 minutes at 0°-5° C., the cooling bath removed, and stirring continued for 1 hour. The mixture was then poured into 1M hydrochloric acid (15 ml.), and extracted with ethyl-acetate. The combined extracts were dried (MgSO4) and evaporated. The residual oil was purified by flash chromatography on silica gel (50 ml.), eluting with 3:7 v/v ethyl acetate:hexane, to give the title compound (0.18 g., 89%) as a colorless oil; NMR: 1.66(m, 6H), 1.82(m,2H), 3.83(s,3H, CO.OCH3), 3.92(s,3H, OCH3), 3.97(s,2H, CH2.Ar), 5.04(m,1H, --CHO--), 7.09(m, 3H), 7.22(d,1H), 7.42(dd,1H), 7.48(d,1H), 7.57(br,1H), 9.18(br,1H, CONH), 10.57(s,1H, H1 -indole).

Workup

  1. customthe cooling bath removed
  2. stirringstirring
  3. waitcontinued for 1 hour
  4. additionThe mixture was then poured into 1M hydrochloric acid (15 ml.)
  5. extractionextracted with ethyl-acetate
  6. dry with materialThe combined extracts were dried (MgSO4)
  7. customevaporated
  8. customThe residual oil was purified by flash chromatography on silica gel (50 ml.)
  9. washeluting with 3:7 v/v ethyl acetate

Sources & evidence

ORD record
ord-3868c81f29f9464b890402d1dd5e67dc
Source dataset
uspto-grants-1996_12
Patent number
US05583152

Reaction notes

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