tert-Butanol → tert-butyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate

HRID 1775771Notes

Reaction equation

HRID 1775771 reaction equation
C(N=C=NC(C)C)(C)C.[C:10]([OH:14])([CH3:13])([CH3:12])[CH3:11].[CH2:15]([O:22][CH2:23][O:24][CH2:25][CH2:26][C@H:27]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C:28](O)=[O:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>[Cu]Cl.ClCCl>[CH2:15]([O:22][CH2:23][O:24][CH2:25][CH2:26][C@H:27]([O:31][Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[C:28]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:29])[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 3

HCID 6386tert-ButanolHCID 12734DiisopropylcarbodiimideHCID 131734748(S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid

Product 1

HCID 131734749tert-butyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoateYield 19%

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

(Step 4) To N,N′-diisopropylcarbodiimide (0.643 mL, 4.13 mmol), tert-butanol (0.415 mL, 4.34 mmol) and copper(I) chloride (20 mg, 0.21 mmol) were added, and the resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was filtered, through Celite (registered trademark), and the solvent in the filtrate was evaporated under reduced pressure. To the obtained residue, dichloromethane (7.4 mL) and (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoic acid (183 mg, 0.516 mmol) obtained in Step 3 were added, and the resulting mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered through Celite (registered trademark), and the solvent of the filtrate was evaporated under reduced pressure. The resulting residue was purified by thin-layer chromatography (ethyl acetate/n-hexane=1/20), whereby tert-butyl (S)-4-(benzyloxymethoxy)-2-(tert-butyldimethylsiloxy)butanoate (40 mg, 19%) was obtained.

Workup

  1. filtrationThe reaction mixture was filtered, through Celite (registered trademark)
  2. customthe solvent in the filtrate was evaporated under reduced pressure
  3. stirringthe resulting mixture was stirred at room temperature for 24 hours
  4. filtrationThe reaction mixture was filtered through Celite (registered trademark)
  5. customthe solvent of the filtrate was evaporated under reduced pressure
  6. customThe resulting residue was purified by thin-layer chromatography (ethyl acetate/n-hexane=1/20)

Sources & evidence

ORD record
ord-cd918a7044354a3baf6dff715b45429a
Source dataset
uspto-grants-2016_02
Patent number
US09260459B2

Reaction notes

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