HCID 86638632, compound → HCID 67083654, compound

HRID 516914Notes

Reaction equation

HRID 516914 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-99b5016e3fdc496eb4c6d69ea64087cd
Source dataset
uspto-grants-2015_08
Patent number
US09115087B2

Reaction notes

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