Water → farnesylamine

HRID 488157Notes

Reaction equation

HRID 488157 reaction equation
O.[CH3:2]/[C:3](/[CH2:9][CH2:10]/[CH:11]=[C:12](\[CH3:19])/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:4]\[CH2:5][N:6]=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[CH3:2]/[C:3](/[CH2:9][CH2:10]/[CH:11]=[C:12](\[CH3:19])/[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:4]\[CH2:5][NH2:6]

Participants

5

Reactant 3

HCID 962Water2×HCID 11776TriphenylphosphineHCID 10014874HCID 10014874, compound

Product 1

HCID 6449783farnesylamine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Water (46 μL) was added to a stirred mixture of (E,E)-3,7,11-trimethyl-2,6,10-dodecatrienylazide (0.8 g, 3.2 mmol) and triphenylphosphine (0.94 g, 3.62 mmol) in THF (3 mL) and stirred at room temperature overnight. An additional amount of water (46 ML) was added and stirred for another two hours. The reaction mixture was evaporated to dryness and the residue was redissolved in methylene chloride, then MgSO4 was added and filtered. The filtrate was concentrated in vacuo to give the crude title compound as an oily solid which was used in the next step without purification.

Workup

  1. stirringstirred for another two hours
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe residue was redissolved in methylene chloride
  4. additionMgSO4 was added
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-d0a60b80fcd24b76a175e444d58de7ed
Source dataset
uspto-grants-1994_03
Patent number
US05298655

Reaction notes

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