Hydroxide → (R)-5-Amino-3-(pyrrolidin-2-ylmethyl)-1H-indole

HRID 1683928Notes

Reaction equation

HRID 1683928 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.[OH-]>C(O)C.[Pd]>[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

5

Reactant 2

HCID 961HydroxideHCID 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 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of (R)-3-(N-benzyloxycarbonylpyrrolidin-2-ylmethyl)-5-dibenzylamino-1H-indole (7.90 g, 14.91 mmol) and moist palladium (ll) hydroxide on carbon (Peariman's catalyst, 3.16 g) in absolute ethanol (100 mL) was shaken under a hydrogen atmosphere (3 arm) 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-bb0614393adc472087663cc2838bac96
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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