HCID 89657462, compound → HCID 89657501, compound

HRID 1775240Notes

Reaction equation

HRID 1775240 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@:12]1([C:17]1[NH:18][C:19]2[CH:20]=[CH:21][CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[C:24]=2[CH:25]=1)[CH3:16])=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[CH3:16][C@:12]1([C:17]2[NH:18][C:19]3[CH:20]=[CH:21][CH:22]=[C:23]([C:26]([O:28][CH3:29])=[O:27])[C:24]=3[CH:25]=2)[CH2:13][CH2:14][CH2:15][NH:11]1

Participants

5

Reactant 2

HCID 89657462HCID 89657462, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89657501HCID 89657501, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A stirred mixture of (R)-methyl 2-(1-(benzyloxycarbonyl)-2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate (307 mg, 0.78 mol), methanol (10 mL), and 10% palladium on carbon (50 mg) was treated with a balloon-pressure of hydrogen at room temperature. After 2 hours, the mixture was filtered through Celite and the filtrate was concentrated to give (R)-methyl 2-(2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate (190 mg, 94%). 1H NMR (CDCl3-d1) δ 10.9 (s, 1H), 7.86 (d, 1H, J=7.8 Hz), 7.63 (d, 1H, J=7.8 Hz), 7.24 (t, 1H, J=7.8 Hz), 7.14 (s, 1H), 3.96 (s, 3H), 3.40-3.43 (m, 1H), 3.12-3.15 (m, 1H), 2.78-2.81 (m, 1H), 2.23-2.26 (m, 3H), and 1.94 (s, 3H). MS (ESI) m/e [M+1]+ 259.0.

Workup

  1. filtrationthe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-469b68e53f274f60a88060b13bd9e977
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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