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

HRID 744135Notes

Reaction equation

HRID 744135 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-0262fda25972404a91d5a217f264afa3
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

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