Potassium Carbonate → potassium (R)-((4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl)methyl)trifluoroborate

HRID 1621608Notes

Reaction equation

HRID 1621608 reaction equation
Br[CH2:2][B-:3]([F:6])([F:5])[F:4].[K+:7].[C:8]([N:15]1[CH2:20][CH2:19][NH:18][C@H:17]([CH3:21])[CH2:16]1)([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].C([O-])([O-])=O.[K+].[K+]>C1COCC1>[C:11]([O:10][C:8]([N:15]1[CH2:20][CH2:19][N:18]([CH2:2][B-:3]([F:6])([F:5])[F:4])[C@H:17]([CH3:21])[CH2:16]1)=[O:9])([CH3:14])([CH3:12])[CH3:13].[K+:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2756811(R)-1-Boc-3-methylpiperazineHCID 23690312Potassium (bromomethyl)trifluoroborate

Product 1

HCID 71501915potassium (R)-((4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl)methyl)trifluoroborateYield 94.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of potassium (bromomethyl)trifluoroborate (1.20 g, 5.38 mmol) and (R)-4-N-Boc-2-methyl-piperazine (1.166 g, 5.65 mmol) in THF (7.00 mL) was heated at 80° C. under nitrogen for 24 h. After cooling, the mixture was concentrated, re-dissolved in acetone (125 mL) and treated with K2CO3 (1 eq). The suspension was stirred for 30 min and filtered through a short plug of Celite® (diatomaceous earth), washing with additional acetone and the combined organic phases were concentrated to give potassium (R)-((4-(tert-butoxycarbonyl)-2-methylpiperazin-1-yl)methyl)trifluoroborate as a pale yellow foam (1.627 g, 94%). 19F-NMR (377 MHz, d6-acetone) δ −141.36.

Workup

  1. temperatureAfter cooling
  2. concentrationthe mixture was concentrated
  3. dissolutionre-dissolved in acetone (125 mL)
  4. filtrationfiltered through a short plug of Celite® (diatomaceous earth)
  5. washwashing with additional acetone
  6. concentrationthe combined organic phases were concentrated

Sources & evidence

ORD record
ord-8978bc47c1764a129d7958e13b0657c4
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

Loading…