N-Methylbenzylamine → HCID 975398, compound

HRID 2042965Notes

Reaction equation

HRID 2042965 reaction equation
[CH2:1]([NH:8][CH3:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:10]1[CH2:14][CH2:13][CH2:12][C@@H:11]1[C:15]([OH:17])=O.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[CH2:1]([N:8]([CH3:9])[C:15]([C@H:11]1[CH2:12][CH2:13][CH2:14][O:10]1)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 7669N-MethylbenzylamineHCID 516892Sodium BicarbonateHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734707Tetrahydro-2-furoic acid, (+)-

Product 1

HCID 975398HCID 975398, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

25.30 g of N-benzyl-N-methylamine are added to a solution of 20.00 ml of (R)-tetrahydrofuran-2-carboxylic acid in 200 ml tetrahydrofuran. Then a total of 67.10 g of O-(benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate are added batchwise while cooling with an ice bath and the reaction mixture is then stirred for about 48 hours at ambient temperature. The precipitate formed is suction filtered, the filtrate is evaporated, mixed with water and filtered again. The filtrate obtained is made alkaline with sodium hydrogen carbonate solution and extracted with ethyl acetate. The combined ethyl acetate extracts are washed with water and saturated sodium chloride solution, dried over magnesium sulfate, and evaporated down. A yellowish oil remains, which is further reacted without any further purification. Yield: 24.60 g (54% of theory); mass spectrum (ESI+): m/z=220 [M+H]+; Rf value: 0.62 (silica gel, ethyl acetate).

Workup

  1. temperaturewhile cooling with an ice bath
  2. customThe precipitate formed
  3. filtrationfiltered
  4. customthe filtrate is evaporated
  5. additionmixed with water
  6. filtrationfiltered again
  7. customThe filtrate obtained
  8. extractionextracted with ethyl acetate
  9. washThe combined ethyl acetate extracts are washed with water and saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customevaporated down
  12. customA yellowish oil remains, which is further reacted without any further purification

Sources & evidence

ORD record
ord-34ca05f9e92f45d295a863adf428edae
Source dataset
uspto-grants-2013_11
Patent number
US08586608B2

Reaction notes

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