(2S)-2,5-Dihydro-2-isopropyl-3,6-dimethoxypyrazine → HCID 57779792, compound

HRID 1364192Notes

Reaction equation

[CH3:1][O:2][C:3]1[C@H:4]([CH:11]([CH3:13])[CH3:12])[N:5]=[C:6]([O:9][CH3:10])[CH2:7][N:8]=1.C([Li])CCC.[F:19][C:20]([F:31])([F:30])[O:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24]Br>O1CCCC1.[NH4+].[Cl-]>[CH:11]([C@H:4]1[C:3]([O:2][CH3:1])=[N:8][C@H:7]([CH2:24][C:23]2[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=2[O:21][C:20]([F:19])([F:30])[F:31])[C:6]([O:9][CH3:10])=[N:5]1)([CH3:13])[CH3:12]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of (2S)-(+)-2,5-dihydro-3,6-dimethoxy-2-isopropylpyrazine (7.2 g, 39.4 mmol) in tetrahydrofuran (50 mL) was cooled to −78° C. A solution of n-butyllithium in hexanes (2.5 M, 18.9 mL, 47.2 mmol) was added dropwise, and stirring was continued for 15 minutes. 2-Trifluoromethoxybenzyl bromide (10.0 g, 39.4 mmol) was added, and the resulting mixture was maintained at −78° C. for 30 minutes, then allowed to slowly warm to room temperature. The reaction was then diluted with saturated aqueous NH4Cl solution and extracted with ethyl acetate. The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (100% hexanes) to give the desired product.

Workup

temperatureto slowly warm to room temperature
extractionextracted with ethyl acetate
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customto give an oil that
customwas purified via flash chromatography on silica gel (100% hexanes)

Sources & evidence

ORD record: ord-a9ca2d5472c0412d8608855df59b18bf
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888345B2

Reaction notes

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