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N-Boc-5-bromoindole → 5-[(1-Tert-butoxycarbonyl-2-propyl-pyrrolidin-2-yl)-hydroxy-methyl]-indole-1-carboxylic acid tert-butyl ester

HRID 661559
Notes
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Reaction equation

HRID 661559 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 666875405-[(1-Tert-butoxycarbonyl-2-propyl-pyrrolidin-2-yl)-hydroxy-methyl]-indole-1-carboxylic acid tert-butyl esterYield 43%

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

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-f112b194ae474319ad38af7ed2112dea
Source dataset
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08084623B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes