(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-5-dibenzylamino-1H-indole → (R)-5-Amino-3-(pyrrolidin-2-ylmethyl)-1H-indole

HRID 1440224Notes

Reaction equation

HRID 1440224 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([N:26](CC3C=CC=CC=3)CC3C=CC=CC=3)[CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:16][C@H:12]1[CH2:13][CH2:14][CH2:15][NH:11]1

Participants

4

Reactant 1

HCID 9984453(R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-5-dibenzylamino-1H-indole

Product 1

HCID 10262726(R)-5-Amino-3-(pyrrolidin-2-ylmethyl)-1H-indoleYield 100%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-5-dibenzylamino-1H-indole (7.90 g, 14.91 mmol) and moist palladium (II) hydroxide on carbon (Pearlman's catalyst, 3.16 g) in absolute ethanol (100 mL) was shaken under a hydrogen atmosphere (3 atm) for 12 hours at room temperature. The resulting mixture was filtered through diatomaceous earth, and the filtrate was evaporated and dried under reduced pressure to afford the title compound as a white foam (3.20 g, 100%): 1H NMR (CD3OD) δ7.18 (d, J=8.5 Hz, 1H), 7.08 (s, 1H), 6.92 (d, J=2.0 Hz, 1H), 6.69 (dd, J=1.9 and 8.5 Hz, 1H), 3.81-3.69 (m, 1H), 3.30-2.95 (m, 4H), 2.09-1.55 (m, 4H); 13C NMR (CD3OD) δ140.1, 133.4, 129.1, 125.0, 114.6, 113.1, 109.8, 105.1, 62.1, 46.0, 31.1, 29.1, 24.3; LRMS (m/z, relative intensity) 215 (M+, 2), 198 (1) , 146 (100), 128 (7), 117 (9), 70 (60).

Workup

  1. filtrationThe resulting mixture was filtered through diatomaceous earth
  2. customthe filtrate was evaporated
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-78dc637156c04f8f9de637274a58ddc2
Source dataset
uspto-grants-1996_03
Patent number
US05498626

Reaction notes

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