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

HRID 895692Notes

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

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. C. 2-(S)-[1-(S)-o-tolyl-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid

Workup

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

Sources & evidence

ORD record: ord-47d1b1bbf2b64aeab838552f16777c69
Source dataset: uspto-grants-2005_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06916830B2

Reaction notes

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