Sodium Azide → HCID 58092780, compound

HRID 1807682Notes

Reaction equation

HRID 1807682 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH3:5][O:6][C:7]([C@@H:9]1[C@H:13]([CH2:14]I)[CH2:12][CH2:11][N:10]1[C@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH3:17])=[O:8]>CN(C=O)C>[CH3:5][O:6][C:7]([C@@H:9]1[C@H:13]([CH2:14][N:1]=[N+:2]=[N-:3])[CH2:12][CH2:11][N:10]1[C@H:16]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH3:17])=[O:8]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 58092804HCID 58092804, compound

Product 1

HCID 58092780HCID 58092780, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium azide (5.34 mmol) was added to a solution of (2S,3R)-3-iodomethyl-1-((S)-1-phenyl-ethyl)-pyrrolidine-2-carboxylic acid methyl ester (Stage 36.5) (3.56 mmol) in DMF (30 mL) at rt. After 18 h, the reaction mixture was poured onto water and extracted with MTBE (2×). The combined organic phases were washed with brine, dried (Na2SO4), filtered and concentrated. The residue was purified using a RediSep° silica gel column to to afford the title compound as a brown oil. HPLC: tR=3.26 min (method G); ESI-MS: [M+H]+ 289.

Workup

  1. additionthe reaction mixture was poured onto water
  2. extractionextracted with MTBE (2×)
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-dd6d4e344d3e4dcb9b7badf7a2ef4584
Source dataset
uspto-grants-2013_01
Patent number
US08357707B2

Reaction notes

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