Sodium Azide → tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamate

HRID 2208146Notes

Reaction equation

HRID 2208146 reaction equation
CS(O[C@@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([C@H:6]1[CH2:10][CH2:9][C@H:8]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7]1)=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

Product 1

HCID 86608905tert-butyl [(1S,3S)-3-azidocyclopentyl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Crude product from example C4 is dissolved in dry DMF (180 mL). After addition of sodium azide (11.7 g; 180.0 mmol) the reaction mixture is stirred for three days at 60° C. After filtration the reaction mixture is concentrated under reduced pressure, diluted with dichloromethane, extracted with water, half saturated brine and dried over MgSO4. After column chromatography on silica gel (cyclohexane/AcOEt—9:1) 11.8 g of the title compound is obtained as pale yellow oil.

Workup

  1. filtrationAfter filtration the reaction mixture
  2. concentrationis concentrated under reduced pressure
  3. additiondiluted with dichloromethane
  4. extractionextracted with water, half saturated brine
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-d0d091f1a2a7424e8db91453c861b326
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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