Water → HCID 19350326, compound

HRID 2063235Notes

Reaction equation

HRID 2063235 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:20]([CH:27]([NH2:33])[CH2:28][CH2:29][N:30]=[N+]=[N-])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].O>C1COCC1>[C:20]([CH:27]([NH2:33])[CH2:28][CH2:29][NH2:30])([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86597516HCID 86597516, compound

Product 1

HCID 19350326HCID 19350326, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A triphenylphosphine (4.8 g; 18.3 mmol) solution in THF (15 mL) is added dropwise to a stirred solution of the above azide in THF (30 mL)/H2O (0.3 mL; 18.3 mmol); the stirring is continued for 24 hrs at r.t. After removal of the solvents to dryness in vacuum, the residue is taken up with a few of EtOH to separate a white precipitate of triphenylphosphine oxide by stirring for 6 hrs at r.t. The final EtOH removal to dryness, at low pressure, gives 3.22 g (18 mmol) of 1-BOC-propane-1,3-diamine as a pale yellow oil.

Workup

  1. customAfter removal of the solvents to dryness in vacuum
  2. customto separate a white precipitate of triphenylphosphine oxide
  3. customThe final EtOH removal to dryness

Sources & evidence

ORD record
ord-e73d7c5e14b246a5a5c2fc93eb5469cd
Source dataset
uspto-grants-2012_10
Patent number
US08288368B2

Reaction notes

Loading…