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

HRID 447650Notes

Reaction equation

HRID 447650 reaction equation
CS(O[C@H:6]1[CH2:10][C@@H:9]([CH2:11][OH:12])[C@@H:8]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:7]1)(=O)=O.CN(C)C=O.[N-:26]=[N+:27]=[N-:28].[Na+]>>[N:26]([C@@H:6]1[CH2:10][C@@H:9]([CH2:11][OH:12])[C@@H:8]([O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH2:7]1)=[N+:27]=[N-:28]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 86618728(1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-(hydroxymethyl)cyclopentyl methanesulfonate

Product 1

HCID 59671297((1S,2S,4R)-4-azido-2-{[tert-butyl(dimethyl)silyl]oxy}cyclopentyl)methanol

Conditions

Temperature
55 °C

Procedure

To a solution of (1S,3S,4S)-3-{[tert-butyl(dimethyl)silyl]oxy}-4-(hydroxymethyl)-cyclopentyl methanesulfonate (0.470 g, 0.00145 mol) in N,N-Dimethylformamide (6 mL, 0.08 mol) was added sodium azide (0.4 g, 0.006 mol) 23° C., 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 Et20 (3×), dried (Na2SO4), filtered and concentrated. The residue was purified by flash chromatography (10 to 25% ethyl acetate/hexane) to obtain 211 mg (53.7%).

Workup

  1. temperatureThe reaction was cooled to 23° C.
  2. customquenched by addition of water
  3. extractionextracted with Et20 (3×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10 to 25% ethyl acetate/hexane)
  8. customto obtain 211 mg (53.7%)

Sources & evidence

ORD record
ord-89215ba9a8ef47f1b432026025fb9ed8
Source dataset
uspto-grants-2013_07
Patent number
US08481550B2

Reaction notes

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