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Ammonium Chloride → (2S,5R)-2-[2-(2-Chloro-phenyl)-ethyl]-5-isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine

HRID 1911550
Notes
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Reaction equation

HRID 1911550 reaction equation
[CH3:1][O:2][C:3]1[C@@H:4]([CH:12]([CH3:14])[CH3:13])[N:5]=[C:6]([O:10][CH3:11])[CH:7]([CH3:9])[N:8]=1.C([Li])(C)(C)C.Br[CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:29].[Cl-].[NH4+]>O1CCCC1>[Cl:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[CH2:22][CH2:21][C@@:7]1([CH3:9])[C:6]([O:10][CH3:11])=[N:5][C@H:4]([CH:12]([CH3:14])[CH3:13])[C:3]([O:2][CH3:1])=[N:8]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 27569631-(2-Bromoethyl)-2-chlorobenzeneHCID 11481040(R)-(-)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-methylpyrazineHCID 178418306HCID 178418306, compound

Product 1

HCID 68716087(2S,5R)-2-[2-(2-Chloro-phenyl)-ethyl]-5-isopropyl-3,6-dimethoxy-2-methyl-2,5-dihydro-pyrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (R)-(−)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-methylpyrazine (1.0 g, 5.0 mmol) in tetrahydrofuran (23 ml) was cooled to −70° C., then tert.butyllithium (1.7 M in pentane, 3.26 ml, 5.55 mmol) was added and the mixture was stirred for 1 hour. A solution of 1-(2-bromo-ethyl)-2-chlorobenzene (1.44 g, 6.56 mmol) in tetrahydrofuran (10 ml) was added slowly and the mixture was stirred overnight at −70° C. At room temperature saturated ammonium chloride solution was added and the mixture was extracted three times with ether. The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1 to yield an orange solid, (1.22 g, 72%); MS (ISP): 337.1; 339.1 ((M+H)+.).

Workup

  1. stirringthe mixture was stirred overnight at −70° C
  2. extractionthe mixture was extracted three times with ether
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc=1:1
  7. customto yield an orange solid, (1.22 g, 72%)

Sources & evidence

ORD record
ord-1f8d0e6aa34744169bd4ce39625a625d
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08604061B2

Reaction notes

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