Borane;tetrahydrofuran → tert-Butyl 4-[2-(hydroxymethyl)phenyl]piperazine-1-carboxylate

HRID 1592741Notes

Reaction equation

HRID 1592741 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20](O)=[O:21])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].B.C1COCC1>C1COCC1>[C:1]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][OH:21])[CH2:12][CH2:13]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 27567762-[4-(tert-Butoxycarbonyl)piperazin-1-yl]benzoic acid

Product 1

HCID 7127802tert-Butyl 4-[2-(hydroxymethyl)phenyl]piperazine-1-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-Boc-4-(2-carboxy-phenyl)-piperazine from Step 1 in 340 mL of THF at 0° C. was added BH3-THF (120 mL of a 1 M solution in THF). The cold bath was removed, and the solution stirred overnight. The solution was cooled to about 0° C. and then 60 mL of 2 M NaOH was added followed by EtOAc and brine. After separation, the aqueous solution was extracted with EtOAc (3×). The combined organic solutions were washed with water (2×) and brine, and then dried (Na2SO4), filtered and concentrated to give about 11.2 g (38.3 mmol, 96%) of the title compound. LRMS (ESI+): 393.2 [M+1]

Workup

  1. customThe cold bath was removed
  2. addition60 mL of 2 M NaOH was added
  3. customAfter separation
  4. extractionthe aqueous solution was extracted with EtOAc (3×)
  5. washThe combined organic solutions were washed with water (2×) and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a0535a3e7ffd48fab415df0a67ac95f8
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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