N-[(Methanesulfonyl)oxy]-N-methylmethanamine → HCID 178506778, compound

HRID 2303742Notes

Reaction equation

HRID 2303742 reaction equation
[CH:1]1([Li:6])[CH:5]=[CH:4][CH:3]=[CH:2]1.[N:7](OS(C)(=O)=O)([CH3:9])[CH3:8].C([Li])CCC>C1COCC1.CCCCCC>[CH3:8][N:7]([C:1]1([Li:6])[CH:5]=[CH:4][CH:3]=[CH:2]1)[CH3:9]

Participants

6

Reactant 3

HCID 12679266N-[(Methanesulfonyl)oxy]-N-methylmethanamineHCID 178418339ButyllithiumHCID 178506819HCID 178506819, compound

Product 1

HCID 178506778HCID 178506778, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent2×

Conditions

Temperature
-20 °C

Procedure

A solution of 3 g of cyclopentadienyllithium (0.042 moles) in 30 ml of THF was added slowly at −30° C. to a solution of 5.9 g of compound 6 (0.042 moles) in 20 ml of THF. The mixture was then heated to −20° C. and stirred for 30 min. Hexane was then added and the solution was filtered. 1.8 ml of a 2.3 molar solution of butyllithium (0.042 moles) in hexane were then added at −20° C. to produce a precipitate. The precipitate was filtered off and washed with twice 20 ml of hexane. After drying under vacuum, 2.0 g (40% of the theoretical yield) of compound 7 were obtained in the form of a white powder; cf. Angew. Chem., Int. Ed. Engl. 19, (1980), 1010. 1H NMR (400 MHz, THF): δ=5.34 (bd, J=2.2 Hz, 2H); 5.15 (bd, J 2.2 Hz, 2H); 2.56 (s, 6H).

Workup

  1. filtrationthe solution was filtered
  2. customto produce a precipitate
  3. filtrationThe precipitate was filtered off
  4. washwashed with twice 20 ml of hexane
  5. customAfter drying under vacuum, 2.0 g (40% of the

Sources & evidence

ORD record
ord-afb8eb9144dd4edd9e3a44549c3a8a9c
Source dataset
uspto-grants-2002_08
Patent number
US06433112B1

Reaction notes

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