Benzyl succinimido carbonate → (R)-Benzyl methyl(1,2,3,4-tetrahydroquinolin-3-yl)carbamate

HRID 1530768Notes

Reaction equation

HRID 1530768 reaction equation
[CH3:1][NH:2][C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4]1.[CH2:13]([O:20][C:21](ON1C(=O)CCC1=O)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)/C=C\C(O)=O.CN[C@@H]1CC2C(=CC=CC=2)NC1>C1(C)C=CC=CC=1>[CH3:1][N:2]([C@@H:3]1[CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][CH2:4]1)[C:21](=[O:22])[O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 83172Benzyl succinimido carbonateHCID 99217293-Quinolinamine, 1,2,3,4-tetrahydro-N-methyl-, (R)-, (Z)-2-butenedioate (1:1)HCID 9921730(R)-N-Methyl-1,2,3,4-tetrahydroquinolin-3-amine

Product 1

HCID 10827786(R)-Benzyl methyl(1,2,3,4-tetrahydroquinolin-3-yl)carbamate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of (R)-1,2,3,4-tetrahydro-N-methyl-3-quinolinamine of crude material prepared above (V, EXAMPLE 4, 15.0 g), approximately 84.4 mmol) in toluene (50 ml) is stirred at −40° while N-(benzyloxycarbonyloxy)succinimide (24.2 g, 97.1 mmol) in toluene (150 ml) is added over one hr. After 30 min at −40°, GLC analysis indicated that all of (V) had been consumed. The mixture is quenched by the addition of sodium bicarbonate (10% aqueous solution, 300 ml) and warmed to 0°, followed by the addition of methanol (100 ml). This is stirred overnight and then extracted with ethyl acetate. Drying over magnesium sulfate and solvent removal gives a liquid which is purified by flash chromatography (230-400 mesh silica gel; hexane/ethyl acetate, 4/1) which crystallized from ethyl acetate/hexane to give the title compound, mp=80°; NMR (CDCl3) 2.88, 2.80-3.04, 3.30, 3.83, 4.57, 5.16, 6.51, 6.64, 6.96-7.02 and 7.35 δ; [a]25D=−50.1° (CH3OH, c=0.816); IR (mineral oil) 1680 and 1606 cm−1.

Workup

  1. additionis added over one hr
  2. customhad been consumed
  3. customThe mixture is quenched by the addition of sodium bicarbonate (10% aqueous solution, 300 ml)
  4. temperaturewarmed to 0°
  5. additionfollowed by the addition of methanol (100 ml)
  6. extractionextracted with ethyl acetate
  7. dry with materialDrying over magnesium sulfate and solvent removal
  8. customgives a liquid which
  9. customis purified by flash chromatography (230-400 mesh silica gel; hexane/ethyl acetate, 4/1) which
  10. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-b33e893e3f2449b1b593edb1d5e8e02f
Source dataset
uspto-grants-2001_03
Patent number
US06197339B1

Reaction notes

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