Triethylamine → HCID 69676595, compound

HRID 1751670Notes

Reaction equation

Br[CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:13])[C:8]=2[F:12])[C:3]1=[O:14].[C:15]([O:19][C:20]([N:22]1[CH2:26][CH2:25][CH2:24][C@H:23]1[C:27]([OH:29])=[O:28])=[O:21])([CH3:18])([CH3:17])[CH3:16].C(N(CC)CC)C>CC#N.CCOC(C)=O>[N:22]1([C:20]([O:19][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:21])[CH2:26][CH2:25][CH2:24][CH:23]1[C:27]([O:29][C@H:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:13])[C:8]=2[F:12])[C:3]1=[O:14])=[O:28]

Participants

Conditions

Temperature: 55 °C

Procedure

To a solution of 2,6-dibromo-5-fluoro-3,4-dihydronaphthalen-1(2H)-one in MeCN (30 mL) was added (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (1.12 g, 5.2 mmol) and triethyl amine (0.62 mL, 4.48 mmol) and the solution was heated to 55° C. After stirring for 15 h, the solution was cooled to rt, and diluted with EtOAc and washed successively with saturated aqueous NaHCO3 and brine. The organics were dried over MgSO4, filtered and concentrated under reduced pressure. The crude residue was purified by silica column chromatography (10% to 35% EtOAc/hexanes) to afford (2S)-2-(6-bromo-5-fluoro-1-oxo-1,2,3,4-tetrahydronaphthalen-2-yl) 1-tert-butyl pyrrolidine-1,2-dicarboxylate (648 mg, 38%).

Workup

temperaturethe solution was cooled to rt
washwashed successively with saturated aqueous NaHCO3 and brine
dry with materialThe organics were dried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude residue was purified by silica column chromatography (10% to 35% EtOAc/hexanes)

Sources & evidence

ORD record: ord-cb180d53a50d44f5a48173e33ad1052c
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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