tert-Butyl bromoacetate → HCID 60684633, compound

HRID 1432034Notes

Reaction equation

HRID 1432034 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7]Br)([CH3:4])([CH3:3])[CH3:2].[NH:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][OH:17].C(N(C(C)C)CC)(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:9])[CH2:7][N:10]1[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]1[CH2:16][OH:17])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 94263Piperidin-2-ylmethanol

Product 1

HCID 60684633HCID 60684633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Bromo-acetic acid tert-butyl ester (0.39 g, 2 mmol) was dissolved in DMF (1 mL). A solution of piperidin-2-yl-methanol (0.25 g, 2.2 mmol) in DMF (1 mL) and diisopropylethylamine (0.38 mL, 2.2 mmol) was added. The reaction mixture was stirred at 50° C. for 16 h. The solvent was removed in vacuo. EtOAc (20 mL) and water (7 mL) was added. The two phases were separated. The aqueous phase was extracted twice with EtOAc (20 mL). The combined EtOAc phases were dried over magnesium sulfate, filtered and the filtrate was evaporated in vacuo. The product was isolated as an oil. Yield: 0.37 g, 80%.

Workup

  1. customThe solvent was removed in vacuo
  2. additionEtOAc (20 mL) and water (7 mL) was added
  3. customThe two phases were separated
  4. extractionThe aqueous phase was extracted twice with EtOAc (20 mL)
  5. dry with materialThe combined EtOAc phases were dried over magnesium sulfate
  6. filtrationfiltered
  7. customthe filtrate was evaporated in vacuo
  8. customThe product was isolated as an oil

Sources & evidence

ORD record
ord-38f18d7a1c914394ae799bd95c29cc18
Source dataset
uspto-grants-2009_11
Patent number
US07612068B2

Reaction notes

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