Dimethylformamide → [((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methoxy](tert-butyl)dimethylsilane

HRID 1397629Notes

Reaction equation

HRID 1397629 reaction equation
CS(O[C@H:6]1[CH2:10][C@@H:9]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@@H:8]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:7]1)(=O)=O.CN(C)C=O.[N-:33]=[N+:34]=[N-:35].[Na+]>>[N:33]([C@@H:6]1[CH2:10][C@@H:9]([CH2:11][O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[C@@H:8]([O:20][Si:21]([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22])[CH2:7]1)=[N+:34]=[N-:35]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86618736(1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl methanesulfonate

Product 1

HCID 86618737[((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methoxy](tert-butyl)dimethylsilane

Conditions

Temperature
55 °C

Procedure

To a solution of (1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-({[tert-butyl(dimethyl)silyl]oxy}methyl)cyclopentyl methanesulfonate (2.66 g, 0.00606 mol) in N,N-Dimethylformamide (20 mL, 0.2 mol) was added sodium azide (1.21 g, 0.0186 mol), and the mixture was heated at 55° C. for 3 hours. The reaction was cooled to 23° C., quenched by addition of water and extracted with Et2O (3×), washed with water, brine, dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (0 to 15% ethyl acetate/hexane) to obtain 2.13 g (91.1%).

Workup

  1. temperatureThe reaction was cooled to 23° C.
  2. customquenched by addition of water
  3. extractionextracted with Et2O (3×)
  4. washwashed with water, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography (0 to 15% ethyl acetate/hexane)
  9. customto obtain 2.13 g (91.1%)

Sources & evidence

ORD record
ord-5dcdf7ff1a7d41c5bcb0f10002e662f7
Source dataset
uspto-grants-2014_12
Patent number
US08901136B2

Reaction notes

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