Triethylamine → 5-Methoxy-3-{[(2R)-1-methyl-2-pyrrolidinyl]methyl}-1H-indole

HRID 975011Notes

Reaction equation

HRID 975011 reaction equation
C(OC(N1CCC[C@@H]1C([N:18]1[C:26]2[C:21](=[CH:22][C:23]([O:27][CH3:28])=[CH:24][CH:25]=2)[CH:20]=[CH:19]1)=O)=O)C1C=CC=CC=1.[CH2:29]([N:31]([CH2:34][CH3:35])[CH2:32][CH3:33])C.[C:36](OCC)(=O)C>>[CH3:28][O:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[NH:18][CH:19]=[C:20]2[CH2:33][C@H:32]1[CH2:36][CH2:35][CH2:34][N:31]1[CH3:29]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 53836935HCID 53836935, compound

Product 1

HCID 98813245-Methoxy-3-{[(2R)-1-methyl-2-pyrrolidinyl]methyl}-1H-indoleYield 13%

Procedure

(R)-(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-methoxy-1H-indole was used. The chromatographic eluent was 8% triethylamine in ethyl acetate to afford the title compound (yields ranged from 13 to 61%) as an oil whose spectral and physical properties were identical with the spectral and physical properties of the title compound of Example 1A with the exception of specific rotation of plane polarized light: [α]25D =+100° (CHCl3, c=1.0). HRMS: calculated for C15H20N2O: 244.1573; found: 244.1547.

Sources & evidence

ORD record
ord-c6012a9df694438998901fc923927b2f
Source dataset
uspto-grants-1997_03
Patent number
US05607951

Reaction notes

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