Ethyl bromoacetate → HCID 86626521, compound

HRID 604210Notes

Reaction equation

HRID 604210 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([CH2:7][NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:3][CH2:2]1.C(N(CC)CC)C.Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>O1CCCC1.O.[Cl-].[Na+].O>[C:11]([O:10][C:9]([NH:8][CH2:7][CH:4]1[CH2:5][CH2:6][N:1]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:2][CH2:3]1)=[O:15])([CH3:12])([CH3:14])[CH3:13]

Participants

7

Reactant 3

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamate

Product 1

HCID 86626521HCID 86626521, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tert-butyl piperidine-4-ylmethyl-carbamate (2.00 g) is dissolved in tetrahydrofuran (10 ml), and thereto is added triethylamine (1.69 ml), followed by an addition dropwise of ethyl bromoacetate (1.24 mL) in water bath and the mixture is stirred at room temperature for 2 hours. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate. The organic layer is washed twice with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure, and to the resulting crystalline residue is added isopropylether and the mixture is filtered to give ethyl [4-(tert-butoxy-carbonylamino-methyl)-piperidin-1-yl]-acetate (1.87 g). MS (m/z): 301 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe organic layer is washed twice with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionto the resulting crystalline residue is added isopropylether
  6. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-70d3c8786fce4770be4026127baa4953
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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