Water → HCID 10041705, compound

HRID 465571Notes

Reaction equation

HRID 465571 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>O1CCCC1>[NH2:1][CH2:4][CH2:5][CH2:6][CH2:7][CH:8]([CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)[CH2:9][C:10]([CH3:16])([CH3:15])[C:11]([O:13][CH3:14])=[O:12]

Participants

5

Reactant 3

HCID 962Water2×HCID 11776Triphenylphosphine2×HCID 10360281HCID 10360281, compound

Product 1

HCID 10041705HCID 10041705, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude azide (1.29 g) is dissolved in 7 ml dry tetrahydrofuran, and 0.82 g (3.1 mmol) triphenylphosphine is added followed by two boiling stones and 0.08 ml (4.4 mmol) water. The solution is stirred for 14 h. An additional 0.82 g triphenylphosphine and 0.08 ml water are added and the mixture is stirred for another 5 h. The reaction mixture is concentrated under vacuum and then purified by silica gel chromatography using first ethyl acetate to remove nonpolar impurities and triphenylphosphine oxide. Then the eluent is changed to 9:1 methanol/triethylamine to obtain methyl 8-amino-2,2-dimethyl-4-(3-[3-pyridyl)propyl]-octanoate as an oil; NMR (CDCl3): delta 3.59 (s,3H), 2.67 (t,2H), 2.54 (t,2H), 1.13 (s,6H).

Workup

  1. stirringthe mixture is stirred for another 5 h
  2. concentrationThe reaction mixture is concentrated under vacuum
  3. custompurified by silica gel chromatography
  4. customto remove nonpolar impurities and triphenylphosphine oxide

Sources & evidence

ORD record
ord-4c0d35a56adc469e97bda5411eaabd01
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…