Toluene → (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid propan-2-yl ester

HRID 1171853Notes

Reaction equation

HRID 1171853 reaction equation
[C:1]1([C@H:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10][CH2:9][NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19].C1(C)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:22][CH:21]([O:20][C:18]([N:8]1[CH2:9][CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C@@H:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)=[O:19])[CH3:23]

Participants

6

Reactant 4

HCID 1140TolueneHCID 7917Isopropyl chloroformateHCID 11430Potassium CarbonateHCID 1382087(1S)-1,2,3,4-Tetrahydro-1-phenylisoquinoline

Product 1

HCID 67078773(S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid propan-2-yl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
20 °C

Procedure

A 15.00 g portion of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline and 9.22 g of isopropyl chloroformate were added to a mixture of 75 ml of toluene, 10.43 g of potassium carbonate and 45 ml of water and stirred at 20° C. for 2 hours, and then the organic layer was washed with 50 ml of water. The thus obtained organic layer was concentrated under a reduced pressure and then dried to obtain 21.71 g of (S)-1-phenyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylic acid propan-2-yl ester (1H-NMR (DMSO-d6, tetramethylsilane internal standard, 80° C.): δ 1.18 (3H, d, J=6.4 Hz), 1.22 (3H, d, J=6.4 Hz), 2.73-2.93 (2H, m), 3.25-3.34 (1H, m), 3.83-3.92 (1H, m), 4.80-4.91 (1H, m), 6.22 (1H, s), 7.06-7.33 (9H, m), mass spectrum: m/z=296 [M +H]+ (FAB)).

Workup

  1. washthe organic layer was washed with 50 ml of water
  2. concentrationThe thus obtained organic layer was concentrated under a reduced pressure
  3. customdried

Sources & evidence

ORD record
ord-781d1a4fcdcd406282a595e9b5e4a277
Source dataset
uspto-grants-2010_11
Patent number
US07829715B2

Reaction notes

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