Hydrochloric Acid → (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidine

HRID 975696Notes

Reaction equation

HRID 975696 reaction equation
[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([O:12][Si](C(C)(C)C)(C)C)[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])=[O:6])[CH:2]=[CH2:3].Cl.C(OCC)(=O)C.O>O1CCCC1>[CH2:1]([O:4][C:5]([N:7]1[CH2:11][C@H:10]([OH:12])[CH2:9][C@H:8]1[CH2:20][CH2:21][N:22]=[N+:23]=[N-:24])=[O:6])[CH:2]=[CH2:3]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8857Ethyl AcetateHCID 54502598(2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyldimethylsilyloxy) pyrrolidine

Product 1

HCID 53738762(2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidineYield 99.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2R,4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-(t-butyldimethylsilyloxy) pyrrolidine (29.7 g) in tetrahydrofuran was added dropwise 12N hydrochloric acid (15 ml) at ambient temperature. After stirring for 6 hours, the mixture was poured into a mixture of ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted twice with ethyl acetate. The combined organic layer was washed with sat. sodium bicarbonate and brine, dried over magnesium sulfate and evaporated under reduced pressure to give (2R, 4R)-1-allyloxycarbonyl-2-(2-azidoethyl)-4-hydroxypyrrolidine (20.0 g).

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washThe combined organic layer was washed with sat. sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-73651c6de1234a049d5eb5c5d8025df3
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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