Water → HCID 66971245, compound

HRID 1361286Notes

Reaction equation

HRID 1361286 reaction equation
[C:1]([N:8]1[CH2:12][C@@H:11]([N:13]=[N+]=[N-])[CH2:10][C@@H:9]1[CH2:16][CH:17]=[CH2:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CP(C)C.O>C1COCC1>[C:1]([N:8]1[CH2:12][C@H:11]([NH2:13])[CH2:10][C@@H:9]1[CH2:16][CH:17]=[CH2:18])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 68983TrimethylphosphineHCID 86636639HCID 86636639, compound

Product 1

HCID 66971245HCID 66971245, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-1-Boc-2-allyl-4-azidopyrrolidine (450 mg, 1.78 mmol) prepared in Step B in THF was added dropwise trimethylphosphine (135 mg, 1.78 mmol). After the reaction mixture was stirred at rt for 5 h, water (0.03 ml) was added, and stirred for additional 20 min. The reaction mixture was concentrated in vacuo, extracted with EtOAc, washed with water and brine, and concentrated in vacuo. The residue was purified by column chromatography(eluent, MeOH/DCM=1/9) to give the title compound (280 mg, 70%).

Workup

  1. stirringstirred for additional 20 min
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. extractionextracted with EtOAc
  4. washwashed with water and brine
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography(eluent, MeOH/DCM=1/9)

Sources & evidence

ORD record
ord-ce81ec8185fd4aef9da25c413392418c
Source dataset
uspto-grants-2011_02
Patent number
US07879852B2

Reaction notes

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