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Triethylamine → (S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

HRID 1919178
Notes
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Reaction equation

HRID 1919178 reaction equation
I[C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:4][CH:3]=1.C(N(CC)CC)C.[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27]>CN(C=O)C.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:29][Si:28]([C:26]#[C:27][C:2]1[NH:6][C:5]([C@@H:7]2[CH2:11][CH2:10][CH2:9][N:8]2[C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])=[N:4][CH:3]=1)([CH3:31])[CH3:30]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 58498756(S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 58498689(S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylateYield 82%

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent

Procedure

A solution of (S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (1 g, 2.75 mmol), triethylamine (1.92 mL, 13.8 mmol) and copper(I) iodide (0.105 g, 0.551 mmol) in DMF (30 mL) was degassed under vacuum and backfilled with nitrogen. Ethynyltrimethylsilane (1.35 g, 13.8 mmol) and Pd(Ph3P)4 (0.159 g, 0.138 mmol) were added and then the reaction was sealed and heated at 50° C. for 1d. The reaction was concentrated to remove the volatiles and the residue was purified on a BIOTAGE® (silica gel, eluted with 0 to 40% ethyl acetate/hexanes) to yield (S)-tert-butyl 2-(5-((trimethylsilyl)ethynyl)-1H-imidazol-2-yl)pyrrolidine-1-carboxylate (751 mg, 2.25 mmol, 82% yield) as brownish foam.

Workup

  1. customthe reaction was sealed
  2. concentrationThe reaction was concentrated
  3. customto remove the volatiles
  4. customthe residue was purified on a BIOTAGE® (silica gel, eluted with 0 to 40% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-babfd1c522f9437c89b7ff1469a0b8a8
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08618153B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes