(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-dibenzylamino-1H-indole → (R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

HRID 744136Notes

Reaction equation

HRID 744136 reaction equation
C(O[C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[C:16]([C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([N:27]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:25]=2)[NH:20][CH:19]=1)=O)=O)C1C=CC=CC=1.C(Cl)Cl.CO.[OH-].[NH4+]>>[CH2:35]([N:27]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:24]1[CH:25]=[C:26]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2[CH2:16][C@H:12]1[CH2:13][CH2:14][CH2:15][N:11]1[CH3:9])[C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 10414998(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-dibenzylamino-1H-indoleHCID 21896990Dichloromethane methanol ammonium hydroxide

Product 1

HCID 10364175(R)-5-dibenzylamino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Procedure

(R)-3 -(N-Benzyloxycarbonylpyrrolidin-2-ylcarbonyl)-5-dibenzylamino-1H-indole was used. Column chromatography using solution with methylene chloride/methanol/ammonium hydroxide [9:1:0.1] afforded the title compound as a pale green foam: 1H NMR (CDCl3) δ7.82 (br s, NH), 7.35-7.19 (m, 10H), 7.20 (d, J=8.6 Hz, 1H), 6.95 (d, J=2.1 Hz, 1H), 6.85 (dd, J=2.3 and 8.7 Hz, 1H), 6.80 (d, J=2.2 Hz, 1H), 4.65 (s, 4H), 3.25-3.02 (m, 2H), 2.52 (dd, J=9.5 and 13.9 Hz, 1H), 2.39-2.15 (m, 2H), 2.30 (s, 3H), 1.85-1.40 (m, 4H); 13C NMR (CDCl3) δ143.2, 139.7, 130.5, 128.5, 128.2, 127.3, 126.8, 122.9, 112.5, 112.2, 111.8, 103.4, 67.0, 57.4, 56.4, 40.6, 31.4, 29.7, 21.9. HRMS: calculated for C28H31N3 409.2520. Found 409.2475.

Sources & evidence

ORD record
ord-f468754339354fea9899ab4fb57c9c2c
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

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