Water → HCID 58297287, compound

HRID 538635Notes

Reaction equation

HRID 538635 reaction equation
[CH3:1][S:2]([N:5]1[CH2:10][CH2:9][CH:8]([NH2:11])[CH2:7][CH2:6]1)(=[O:4])=[O:3].C([O-])([O-])=O.[K+].[K+].[CH2:18]([O:20][C:21](=[O:26])[C:22](Br)([CH3:24])[CH3:23])[CH3:19].O>CN(C=O)C>[CH2:18]([O:20][C:21](=[O:26])[C:22]([NH:11][CH:8]1[CH2:7][CH2:6][N:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][CH2:9]1)([CH3:24])[CH3:23])[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium Carbonate2×HCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl ester2×HCID 113558261-(Methanesulfonyl)piperidin-4-amine

Product 1

HCID 58297287HCID 58297287, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.40 g (13.5 mmol) of 1-methanesulfonyl-piperidin-4-ylamine are dissolved in DMF (32.8 mL). 5.58 g (40.4 mmol) of K2CO3, 3.06 mL (20.2 mmol) ethyl-2-bromoisobutyrate and 1.12 g (6.73 mmol) of KI are added at RT. The reaction is stirred 16 h. Additional ethyl-2-bromoisobutyrate (3.06 mL) and KI (1.12 g) are added and the reaction mixture is stirred for further 16 h. Water and sat. aq. K2CO3 solution is added, the aqueous layer extracted with EE. The combined organic layers are dried over MgSO4 and filtered. The solvent is removed under reduced pressure to afford the crude product, which is purified by silica gel chromatography (eluent: EE/MeOH 95/5) to afford 0.56 g of 2-(1-methanesulfonyl-piperidin-4-ylamino)-2-methyl-propionic acid ethyl ester. Yield: 14%; ESI-MS: 293 [M+H]+; HPLC (Rt): 0.97 min (method E)

Workup

  1. stirringthe reaction mixture is stirred for further 16 h
  2. extractionthe aqueous layer extracted with EE
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. filtrationfiltered
  5. customThe solvent is removed under reduced pressure
  6. customto afford the crude product, which
  7. customis purified by silica gel chromatography (eluent: EE/MeOH 95/5)

Sources & evidence

ORD record
ord-a6ca0c02752b4d00b4b7ed6bab3d8e57
Source dataset
uspto-grants-2014_10
Patent number
US08865744B1

Reaction notes

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