N-Boc-5-bromoindole → HCID 66687540, compound

HRID 1895035Notes

Reaction equation

HRID 1895035 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](Br)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.[C:23]([O:27][C:28]([N:30]1[CH2:34][CH2:33][CH2:32][C:31]1([CH:38]=[O:39])[CH2:35][CH2:36][CH3:37])=[O:29])([CH3:26])([CH3:25])[CH3:24]>CCOCC>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH:38]([C:31]3([CH2:35][CH2:36][CH3:37])[CH2:32][CH2:33][CH2:34][N:30]3[C:28]([O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:29])[OH:39])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 2728482N-Boc-5-bromoindoleHCID 866208602-Formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418306HCID 178418306, compound

Product 1

HCID 66687540HCID 66687540, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of 5-bromo-indole-1-carboxylic acid tert-butyl ester (0.700 g, 2.37 mmol) in ether (20 mL) at −78° C. and under nitrogen was added tert-butyllithium (3.64 mL of 1.43 M solution in pentanes, 5.21 mmol) dropwise. After 30 minutes, a solution of 2-formyl-2-propyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.569 g, 2.37 mmol) in ether (5 mL) was added to the reaction mixture dropwise. The reaction mixture was stirred for one hour, then quenched by the addition of saturated aqueous NH4Cl, and extracted with EtOAc. The combined organic extracts were washed with saturated aqueous NaHCO3 and brine, then dried (MgSO4), filtered and concentrated in vacuo. Purification by chromatography (silica, 0-60% EtOAc in hexanes) gave 5-[(1-tert-butoxycarbonyl-2-propyl-pyrrolidin-2-yl)-hydroxy-methyl]-indole-1-carboxylic acid tert-butyl ester (0.466 g, 1.02 mmol, 43%) as a yellow oil.

Workup

  1. customquenched by the addition of saturated aqueous NH4Cl
  2. extractionextracted with EtOAc
  3. washThe combined organic extracts were washed with saturated aqueous NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography (silica, 0-60% EtOAc in hexanes)

Sources & evidence

ORD record
ord-996931471ad242eaa80c937bf0078b8e
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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