Ammonium Chloride → HCID 22032377, compound

HRID 1792497Notes

Reaction equation

Br[C:2]1[S:3][C:4]([S:7][CH3:8])=[CH:5][CH:6]=1.C([Li])CCC.[CH:14]([CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1)=[O:15].[Cl-].[NH4+]>O1CCCC1.CCCCCC.O>[OH:15][CH:14]([C:2]1[S:3][C:4]([S:7][CH3:8])=[CH:5][CH:6]=1)[CH:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

1.2 g of 2-bromo-5-(methylsulfanyl)thiophen (compound in Production Example 45) was dissolved in 20 mL anhydrous tetrahydrofuran, and 3.72 mL solution of 1.59 M n-butyl lithium in hexane was added dropwise there to at −70° C. After the mixture was stirred for 1 hour, 6 ml solution of 1.2 g t-butyl 4-formyl-piperidine-1-carboxylate in anhydrous tetrahydrofuran was added dropwise thereto and stirred at −70° C. for 2 hours. The temperature of the reaction solution was gradually increased to 0° C., water and an ammonium chloride solution were added thereto, and the reaction solution was extracted with ethyl acetate. The extract was dried over magnesium sulfate and purified by silica gel column chromatography (ethyl acetate/hexane), to give 1.41 g of the title compound as pale pink crystals.

Workup

stirringstirred at −70° C. for 2 hours
extractionthe reaction solution was extracted with ethyl acetate
dry with materialThe extract was dried over magnesium sulfate
custompurified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-d25aea702e9447dabf441251e5cc1cd6
Source dataset: uspto-grants-2006_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07074801B1

Reaction notes

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