Phosgene → HCID 10642837, compound

HRID 1530769Notes

Reaction equation

HRID 1530769 reaction equation
[CH3:1][N:2]([C@@H:13]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:15][CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.[C:30](Cl)(Cl)=[O:31].Cl.[O:35]([NH2:37])[CH3:36]>O1CCCC1.CCOCC.C1(C)C=CC=CC=1>[CH3:1][N:2]([C@@H:13]1[CH2:22][C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:30]([NH:37][O:35][CH3:36])=[O:31])[CH2:14]1)[C:3](=[O:12])[O:4][CH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

8

Reactant 4

HCID 6371PhosgeneHCID 8471Triethylamine2×HCID 521874O-Methylhydroxylamine hydrochlorideHCID 10827786(R)-Benzyl methyl(1,2,3,4-tetrahydroquinolin-3-yl)carbamate

Product 1

HCID 10642837HCID 10642837, compound

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of (R)-methyl-(1,2,3,4-tetrahydro-3-quinolinyl)carbamic acid, phenylmethyl ester (VI, EXAMPLE 5, 3.81 g, 12.86 mmol) and triethylamine (3.9 g, 39 mmol) in dry tetrahydrofuran (50 ml) is added with stirring to a mixture of phosgene (7.1 ml of a 1.93 M toluene solution) in tetrahydrofuran (100 ml) at 0°. After one hour, methoxylamine hydrochloride (2.15 g, 25.7 mmol) and triethylamine (3.9 g, 39 mmol) are added, and the mixture is stirred at 20-25° for two days. The 15 mixture is diluted with ether and washed with water and saline. The organic layer is dried over magnesium sulfate and the solvent is removed under reduced pressure. The residue is sufficiently pure for the next step. An analytical sample is purified via flash chromatography (230-400 mesh silica gel; ethyl acetate/hexane, 50/50) to give the title compound, NMR (CDCl3) 2.88, 2.77-2.97, 3.75, 3.52-4.08, 4.54, 5.13, 7.10-7.27, 7.35 and 7.76 δ; IR (thin film) 1734, 1697 and 1605 cm−1; [a]25D=+38° (CH3OH, c=0.980); MS calculated for C20H23N3O4=369.1688, found=369.1682.

Workup

  1. additionis added
  2. washwashed with water and saline
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. customthe solvent is removed under reduced pressure
  5. customAn analytical sample is purified via flash chromatography (230-400 mesh silica gel; ethyl acetate/hexane, 50/50)

Sources & evidence

ORD record
ord-cadc7c3c2dbe421a81916d4004b26229
Source dataset
uspto-grants-2001_03
Patent number
US06197339B1

Reaction notes

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