Acetic Acid → HCID 86677568, compound

HRID 2401111Notes

Reaction equation

HRID 2401111 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH:20]=O)[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)=[O:5])[CH3:2].ClC(Cl)C.[NH2:26][C:27]1[CH:28]=[CH:29][C:30]([Br:34])=[N:31][C:32]=1[CH3:33].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH2:19][CH2:20][NH:26][C:27]2[C:32]([CH3:33])=[N:31][C:30]([Br:34])=[CH:29][CH:28]=2)[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 144180456-Bromo-2-methylpyridin-3-amineHCID 584784234-(2-Oxoethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester

Product 1

HCID 86677568HCID 86677568, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-oxo-ethyl)-piperidine-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (0.56 g, 1.87 mmol) in 1-2 dichloroethane (DCE, 6 mL) was added 5-amino-2-bromo-6-picoline (0.35 g, 1.87 mmol), acetic acid (3.1 eq) and allowed to stir at room temperature for an hour. NaBH(OAc)3 (3 equiv.) was then added in one portion and the reaction mixture was allowed to stir at room temperature for 16 hours. The reaction was diluted with DCM (10 mL), quenched with 2 M of NH4OH in water (1 mL). The layers were separated, and the aqueous layer was extracted with DCM (10 mL, 2×). The combined organic layers were washed with aqueous NaHCO3 (10 mL), brine (20 mL), dried over Na2SO4, and concentrated under vacuum. Purification over silica gel eluting with ethyl acetate in heptanes (0-75%) afforded 0.44 g (50%) of title compound.

Workup

  1. stirringto stir at room temperature for 16 hours
  2. customquenched with 2 M of NH4OH in water (1 mL)
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with DCM (10 mL, 2×)
  5. washThe combined organic layers were washed with aqueous NaHCO3 (10 mL), brine (20 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customPurification over silica gel eluting with ethyl acetate in heptanes (0-75%)

Sources & evidence

ORD record
ord-ee83e80611864c6b92ec9bef0a4b62c7
Source dataset
uspto-grants-2014_08
Patent number
US08796278B2

Reaction notes

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