Sodium Hydroxide → (2-benzyl-pyrrolidin-2-yl)-(1H-indol-5-yl)-methanone

HRID 1895014Notes

Reaction equation

HRID 1895014 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C:9]1([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:13]([C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[CH:18]2)=[O:14])=O)(C)(C)C.[OH-].[Na+]>Cl.CO>[CH2:24]([C:9]1([C:13]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][CH:19]=[CH:18]3)=[O:14])[CH2:10][CH2:11][CH2:12][NH:8]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 666877772-benzyl-2-(1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 49865934(2-benzyl-pyrrolidin-2-yl)-(1H-indol-5-yl)-methanoneYield 62.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A solution of 2-benzyl-2-(1H-indole-5-carbonyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.045 g, 0.111 mmol) in 1N HCl in MeOH (2.2 mL) was stirred for 14 hours at ambient temperature under nitrogen. Aqueous NaOH (4 N, 0.6 mL) was added and the reaction mixture was extracted into DCM. The combined extracts were washed with brine then dried (MgSO4), filtered and concentrated in vacuo. Purification of the residue by chromatography (silica, 0-10% of a 9:1 MeOH:NH4OH solution in DCM) gave (2-benzyl-pyrrolidin-2-yl)-(1H-indol-5-yl)-methanone (0.021 g, 0.069 mmol, 62%) as a colourless solid, MS=305 [M+H]+.

Workup

  1. extractionthe reaction mixture was extracted into DCM
  2. washThe combined extracts were washed with brine
  3. dry with materialthen dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification of the residue by chromatography (silica, 0-10% of a 9:1 MeOH:NH4OH solution in DCM)

Sources & evidence

ORD record
ord-9f2c5a8002174c8fa928aa04fda9edda
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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