Water → HCID 86757050, compound

HRID 1069040Notes

Reaction equation

HRID 1069040 reaction equation
[N:1]([C@@H:4]1[CH2:8][C@H:7]([OH:9])[CH:6]=[CH:5]1)=[N+:2]=[N-:3].[H-].[Na+].Br[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].O>O1CCCC1>[N:1]([C@@H:4]1[CH2:8][C@H:7]([O:9][CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:6]=[CH:5]1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 14360819HCID 14360819, compound

Product 1

HCID 86757050HCID 86757050, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

(1S-cis)-4-Azido-2-cyclopenten-1-ol (3.4 g) (prepared as described by D. R. Deardorff et al., J. Org. Chem, 1989, 54, 2759) in tetrahydrofuran (60 ml) was added dropwise to a suspension of sodium hydride (1.1 g. of a 60% suspension in oil) in tetrahydrofuran (60 ml) at 0° C. On completion of the addition the mixture was allowed to warm to ambient temperature the added dropwise to a solution of tert-butyl bromoacetate (10.1 ml) in tetrahydrofuran (60 ml) at 0° C. Water (200 ml) was added and the product extracted into ethyl acetate (200 ml) then dried and concentrated. Purification (SiO2, ethyl acetate:isohexane,10:90, as eluent) afforded the subtitle compound (3.6 g).

Workup

  1. customat 0° C
  2. additionOn completion of the addition the mixture
  3. extractionthe product extracted into ethyl acetate (200 ml)
  4. customthen dried
  5. concentrationconcentrated
  6. customPurification (SiO2, ethyl acetate:isohexane,10:90, as eluent)

Sources & evidence

ORD record
ord-afb631d55706437bbd30d3650d4400d7
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

Loading…