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Imidazole → (2S,3R)-tert-Butyl 3-(tert-butyldimethylsilyloxy)-2-cyclopropyl-5-oxopyrrolidine-1-carboxylate

HRID 1011601
Notes
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Reaction equation

HRID 1011601 reaction equation
[CH:1]1([C@H:4]2[C@H:8]([OH:9])[CH2:7][C:6](=[O:10])[N:5]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:3][CH2:2]1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19].N1C=CN=C1>CN(C=O)C>[Si:22]([O:9][C@@H:8]1[CH2:7][C:6](=[O:10])[N:5]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C@H:4]1[CH:1]1[CH2:2][CH2:3]1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:24])[CH3:23]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 57659767(2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate

Product 1

HCID 67313766(2S,3R)-tert-Butyl 3-(tert-butyldimethylsilyloxy)-2-cyclopropyl-5-oxopyrrolidine-1-carboxylateYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

(2S,3R)-tert-Butyl 2-cyclopropyl-3-hydroxy-5-oxopyrrolidine-1-carboxylate (16) (1.34 g, 5.55 mmol) was placed in a flame-dried flask under nitrogen. DMF (12 mL) was added and the mixture stirred until dissolved. tert-butylchlorodimethylsilane (1.06 g, 7.02 mmol) and imidazole (0.558 g, 8.19 mmol) were added and the reaction stirred for 16 hr at rt. DMF was removed in vacuo and EtOAc (100 mL) was added and the organics were washed with sat. NaHCO3 (100 mL), brine (100 mL), dried with sodium sulfate, and concentrated in vacuo. The resulting crude product was purified via column chromatography using EtOAc/hexane gradients to yield (2S,3R)-tert-butyl 3-(tert-butyldimethylsilyloxy)-2-cyclopropyl-5-oxopyrrolidine-1-carboxylate (17) (1.78 g, 90%) as a white solid.

Workup

  1. dissolutionuntil dissolved
  2. stirringthe reaction stirred for 16 hr at rt
  3. customDMF was removed in vacuo and EtOAc (100 mL)
  4. additionwas added
  5. washthe organics were washed with sat. NaHCO3 (100 mL), brine (100 mL)
  6. dry with materialdried with sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe resulting crude product was purified via column chromatography

Sources & evidence

ORD record
ord-82b9dc411bcc47baac316312160e4b01
Source dataset
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07977368B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes