tert-Butyl (2R)-2-bromopropanoate → HCID 60104788, compound

HRID 1836318Notes

Reaction equation

HRID 1836318 reaction equation
[C:1]1([CH3:17])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10][CH2:9][NH:8]1.[C:18]([O:22][C:23](=[O:27])[C@H:24](Br)[CH3:25])([CH3:21])([CH3:20])[CH3:19]>C(#N)C.C(OCC)(=O)C.C(=O)(O)[O-].[Na+]>[C:18]([O:22][C:23](=[O:27])[C@@H:24]([N:8]1[CH2:9][CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:7]1[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[CH3:17])[CH3:25])([CH3:21])([CH3:20])[CH3:19]

Participants

6

Reactant 2

HCID 12882377tert-Butyl (2R)-2-bromopropanoateHCID 16084666HCID 16084666, compound

Product 1

HCID 60104788HCID 60104788, compound

Reagents, catalysts & solvents 3

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
85 °C

Procedure

Racemic 1-o-tolyl-3,4-dihydro-1H-isoquinoline (0.67 g, 3.00 mmol) is added to a solution of (R)-(+)-2-bromo-propionic acid tert-butyl ester (0.50 g, 2.39 mmol) in acetonitrile (10 mL) and the mixture was stirred at 85° C. for 16 hours. After cooling to room temperature the reaction is diluted with ethyl acetate (100 mL) and saturated sodium bicarbonate (100 mL) and the organic layer isolated, washed with water (2×100 mL), brine (1×100 mL), and dried over magnesium sulfate. Filtration and concentration are followed by flash chromatography on SiO2 using 40:1 hexane:ethyl ether to afford 2-(S)-(1-o-tolyl-3,4-dihydro-1H-isoquinolin-2-yl)-propionic acid tert-butyl ester as a colorless syrup.

Workup

  1. temperatureAfter cooling to room temperature the reaction
  2. customthe organic layer isolated
  3. washwashed with water (2×100 mL), brine (1×100 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-dec8a8cc189347c4bd4fb7c9082e6bff
Source dataset
uspto-grants-2004_08
Patent number
US06777422B2

Reaction notes

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