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

HRID 1901554Notes

Reaction equation

HRID 1901554 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-09f79b9be419413caff9f599691caadb
Source dataset
uspto-grants-1996_11
Patent number
US05578612

Reaction notes

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