Borane;tetrahydrofuran → HCID 117952540, compound

HRID 1499201Notes

Reaction equation

HRID 1499201 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:25]=[C:24]([Br:26])[CH:23]=[CH:22][C:18]=2[C:19](O)=[O:20])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1>[Br:26][C:24]1[CH:23]=[CH:22][C:18]([CH2:19][OH:20])=[C:17]([N:14]2[CH2:15][CH2:16][N:11]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:10])[CH2:12][CH2:13]2)[CH:25]=1

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 117942003HCID 117942003, compound

Product 1

HCID 117952540HCID 117952540, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 2-(4-((benzyloxy) carbonyl)piperazin-1-yl)-4-bromobenzoic acid (2 g, 9.1 mmol) in THF (20 mL) was added dropwise BH3/THF (1.0 M, 40 mL) at 0° C. The mixture was refluxed for 2 h, then cooled to RT, quenched with H2O, and extracted with ethyl acetate, 3 N HCl, brine, then dried over Na2SO4, filtered and concentrated. Purification by normal phase silica gel (ethyl acetate/hexanes) provided benzyl 4-(5-bromo-2-(hydroxymethyl)phenyl)piperazine-1-carboxylate as a white solid.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. customquenched with H2O
  3. extractionextracted with ethyl acetate, 3 N HCl, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by normal phase silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-02a008c710be4852b333700f7cbac632
Source dataset
uspto-grants-2015_12
Patent number
US09199994B2

Reaction notes

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