Triethylamine → [4-(Tert-butyldimethylsilanyloxy)-3-hydroxybutyl]carbamic acid tert-butyl ester

HRID 1245771Notes

Reaction equation

HRID 1245771 reaction equation
[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][OH:12])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22]([Si:26]([CH3:29])([CH3:28])Cl)([CH3:25])([CH3:24])[CH3:23]>CN(C)C1C=CN=CC=1.ClCCl>[C:1]([O:5][C:6](=[O:14])[NH:7][CH2:8][CH2:9][CH:10]([OH:13])[CH2:11][O:12][Si:26]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:29])[CH3:28])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 11622550(3,4-Dihydroxybutyl)carbamic acid tert-butyl ester

Product 1

HCID 11508015[4-(Tert-butyldimethylsilanyloxy)-3-hydroxybutyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of (3,4-dihydroxybutyl)carbamic acid tert-butyl ester (2.60 g, 12.7 mmol), triethylamine (2.03 mL, 14.50 mmol) and 4-(dimethylamino)pyridine (0.05 g, 0.4 mmol) in anhydrous dichloromethane (40 mL) at room temperature was added tert-butyldimethylchlorosilane (2.0 g, 13.17 mmol) in one portion. The resulting mixture was stirred at room temperature for 18 hours, washed with water, brine and dried over anhydrous magnesium sulfate. Filtration and concentration in vacuo gave an oil which was purified by column chromatography on silica using ethyl acetate-petroleum ether mixture as eluent to afford a colourless oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationFiltration and concentration in vacuo
  4. customgave an oil which
  5. customwas purified by column chromatography on silica
  6. customto afford a colourless oil

Sources & evidence

ORD record
ord-e0e67e36d2164d3ea4716b057650cf4f
Source dataset
uspto-grants-2006_10
Patent number
US07125904B2

Reaction notes

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