Diisopropylethylamine → HCID 20578892, compound

HRID 1760130Notes

Reaction equation

HRID 1760130 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C@@H:4]([OH:8])[CH:5]([CH3:7])[CH3:6].C(N(C(C)C)CC)(C)C.[CH3:19][Si:20]([CH3:27])([CH3:26])[CH2:21][CH2:22][O:23][CH2:24]Cl>ClCCl>[CH3:1][O:2][C:3](=[O:9])[C@@H:4]([O:8][CH2:24][O:23][CH2:22][CH2:21][Si:20]([CH3:27])([CH3:26])[CH3:19])[CH:5]([CH3:7])[CH3:6]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 11194352Methyl (2S)-2-hydroxy-3-methylbutanoate

Product 1

HCID 20578892HCID 20578892, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of methyl-2-(S)-hydroxy-3-methylbutanoate (1.0 eq; J. Org. Chem. (1997), 62(7), 2292-2297, incorporated herein by reference) in dichloromethane was stirred with diisopropylethylamine (2.0 eq) under nitrogen. 2-Trimethylsilylethoxymethyl chloride (3 eq; Aldrich) was added dropwise via syringe. The solution was stirred at room temperature for 17 hours. The solution was washed with 1.0N HCl, and the water layer was back extracted with dichloromethane. The organics were combined, dried over Na2SO4, and the solvents removed in vacuo. The residue was purified via radial chromatography using 20% ethyl acetate in hexanes affording the title intermediate as a clear oil.

Workup

  1. washThe solution was washed with 1.0N HCl
  2. extractionthe water layer was back extracted with dichloromethane
  3. dry with materialdried over Na2SO4
  4. customthe solvents removed in vacuo
  5. customThe residue was purified via radial chromatography

Sources & evidence

ORD record
ord-c3bdbcea58f6429ebe90ab90c6fc7570
Source dataset
uspto-grants-2005_01
Patent number
US06838455B2

Reaction notes

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