HCID 86638632, compound → HCID 67083654, compound

HRID 1024566Notes

Reaction equation

HRID 1024566 reaction equation
[N:1]([CH:4]([C@H:7]1[CH2:11][CH2:10][CH2:9][O:8]1)[CH2:5][CH3:6])=[N+]=[N-].[H][H]>CCO.CC(O)=O.[Pd]>[O:8]1[CH2:9][CH2:10][CH2:11][CH:7]1[C@H:4]([NH2:1])[CH2:5][CH3:6]

Participants

5

Reactant 2

HCID 86638632HCID 86638632, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67083654HCID 67083654, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18476134Acetic acid ethanolSolvent

Procedure

A solution of (2R)-2-(1-azidopropyl)tetrahydrofuran (1.9 g, 12.24 mmol, 1 equiv) in EtOH/AcOH (105 ml of a 100:5 mixture) and 10% Pd/C CATCart (12.24 mmol, 1 equiv) was placed under a positive pressure of hydrogen for 8 hours. The product mixture was concentrated in vacuo and diluted with DCM. The mixture was passed down a 10 g SCX-2 cartridge (resin loading 0.67 mmol/g), eluting with methanol followed by 2M ammonia in EtOH. The appropriate fractions were concentrated in vacuo to afford the title compound. 1.0 (3H, t, CH3), 1.3 (1H, m), 1.6 (2H, m), 1.9 (3H, m), 2.6 (0.5H, m, CHNH2 of one diastereomer), 2.8 (0.5H, m, CHNH2 of one diastereomer), 3.6 (1H, m, CHO), 3.75 (1H, m, CHO), 3.85 (1H, m, CHO).

Workup

  1. concentrationThe product mixture was concentrated in vacuo
  2. additiondiluted with DCM
  3. washeluting with methanol
  4. concentrationThe appropriate fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-a1e8553f72aa4fca953edfcdc45df558
Source dataset
uspto-grants-2014_05
Patent number
US08722925B2

Reaction notes

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