Ethyl Acetate → HCID 90029693, compound

HRID 2200128Notes

Reaction equation

C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Br:17])[CH:8]=1.[N+](C1C=C[C:24]([C:27]2[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH:28]=2)=C(C(F)(F)F)C=1)([O-])=O.CC[O:46]C(C)=O>C1COCC1>[C:36]([O:35][C:33]([N:30]1[CH2:31][CH2:32][CH:27]([C:24](=[O:46])[C:7]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[C:9]([Br:17])[CH:8]=2)[CH2:28][CH2:29]1)=[O:34])([CH3:39])([CH3:38])[CH3:37]

Participants

Conditions

Temperature: -78 °C

Procedure

Add n-butyllithium (2.5 N, 1.44 mL) to the solution of 1,3-dibromo-5-(trifluoromethyl)benzene (1 g, 3.28 mmol) in THF (15 mL) at −78° C. and stir the mixture at −78° C. for 1 hr. Then add tert-butyl 4-(methoxy(methyl)carbamoyl) piperidine-1-carboxylate (1.4 g, 4.92 mmol) obtained in Step 1 to the mixture and continue stirring. TLC (PE:EtOAc=5:1) shows the reaction is complete. Quench the reaction mixture with saturated ammonium chloride solution. Partition between EtOAc and water, separate the organic layer, and wash with brine, dry over anhydrous sodium sulfate, concentrate to give the crude product. Purify by flash chromatography (silica gel, DCM:MeOH=20:1) to afford the product (387 mg, 27%). MS: (M+1): 436.

Workup

customQuench the reaction mixture with saturated ammonium chloride solution
customPartition between EtOAc and water
customseparate the organic layer
washwash with brine
dry with materialdry over anhydrous sodium sulfate
concentrationconcentrate
customto give the crude product
customPurify by flash chromatography (silica gel, DCM:MeOH=20:1)

Sources & evidence

ORD record: ord-b28f36bf2bec47a2b8a0f8b097babc33
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359338B2

Reaction notes

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