Imidazole → HCID 58557220, compound

HRID 1969564Notes

Reaction equation

HRID 1969564 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([CH2:8][OH:9])[CH2:6][C:5](=[O:10])[CH2:4]1)[CH3:2].N1C=CN=C1.[C:16]([Si:20](Cl)([CH3:22])[CH3:21])([CH3:19])([CH3:18])[CH3:17].CCCCCCC>CN(C=O)C>[Si:20]([O:9][CH2:8][C@@H:7]1[C@H:3]([CH2:1][CH3:2])[CH2:4][C:5](=[O:10])[CH2:6]1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8900HeptaneHCID 28928tert-Butyldimethylsilyl chlorideHCID 58557114HCID 58557114, compound

Product 1

HCID 58557220HCID 58557220, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3R,4S)-3-ethyl-4-(hydroxymethyl)cyclopentanone (2.60 g, 18.3 mmol) in DMF (30 mL) was added imidazole (1.87 g, 27.4 mmol) followed by tert-butylchlorodimethylsilane (3.03 g, 20.1 mmol). After about 4 h, heptane (50 mL) was added. The heptane layer was removed and washed with brine. The brine layer was combined with the DMF layer and extracted with EtOAc/heptane (1:1, 30 mL). The heptane and EtOAc layers were combined, concd in vacuo and purified by chromatography on silica gel eluting with EtOAc/heptane (0-30%) to provide (3S,4R)-3-((tert-butyldimethylsilyloxy)methyl)-4-ethylcyclopentanone (3.5 g, 75%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ 3.77 (dd, J=10.5, 4.3 Hz, 1H), 3.64 (dd, J=10.5, 4.0 Hz, 1H), 2.40-2.20 (m, 5H), 2.18-2.02 (m, 1H), 1.65-1.55 (m, 1H), 1.52-1.37 (m, 1H), 0.97 (t, J=7.4 Hz, 3H), 0.87 (s, 9H), 0.43 (s, 3H), 0.03 (s, 3H).

Workup

  1. customThe heptane layer was removed
  2. washwashed with brine
  3. extractionextracted with EtOAc/heptane (1:1, 30 mL)
  4. custompurified by chromatography on silica gel eluting with EtOAc/heptane (0-30%)

Sources & evidence

ORD record
ord-2b70c749a51e4a56a566287e4f63bcb7
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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