Imidazole → 6-(3-(tert-Butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indole

HRID 2361310Notes

Reaction equation

HRID 2361310 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N:10]3[CH2:14][CH2:13][CH:12]([OH:15])[CH2:11]3)[CH:8]=2)[CH:3]=[CH:2]1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].N1C=CN=C1>CN(C=O)C.CCOC(C)=O>[Si:20]([O:15][CH:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][NH:1]3)=[CH:5][CH:6]=2)[CH2:11]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 679949181-(1H-indol-6-yl)pyrrolidin-3-ol

Product 1

HCID 866815196-(3-(tert-Butyldimethylsilyloxy)pyrrolidin-1-yl)-1H-indoleYield 92%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A homogeneous, colorless solution of 1-(1H-indol-6-yl)pyrrolidin-3-ol (0.1036 g, 0.512 mmol), tert-butylchlorodimethylsilane (0.093 g, 0.615 mmol) and imidazole (0.087 g, 1.281 mmol) in DMF (2.56 mL) was stirred overnight. The mixture was diluted with EtOAc (75 mL), washed with water (4×25 mL) and brine (25 mL) successively, dried over MgSO4, and concentrated in vacuo. The residue was triturated with hexanes to give the desired product (0.1600 g, 0.470 mmol, 92%).

Workup

  1. washwashed with water (4×25 mL) and brine (25 mL) successively
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with hexanes

Sources & evidence

ORD record
ord-df319f2e703c445388c8ee9d65679a7e
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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