Lithium borohydride → Tert-butyl 4-[3-(hydroxymethyl)phenyl]piperazine-1-carboxylate

HRID 595001Notes

Reaction equation

HRID 595001 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([C:20](OCC)=[O:21])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1>[OH:21][CH2:20][C:16]1[CH:15]=[C:14]([N:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:13][CH2:12]2)[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 162179411-Boc-4-(3-(ethoxycarbonyl)phenyl)piperazine

Product 1

HCID 29949342Tert-butyl 4-[3-(hydroxymethyl)phenyl]piperazine-1-carboxylateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl-4-(3-(ethoxycarbonyl)phenyl)piperazine-1-carboxylate (0.20 g, 0.60 mmol) was dissolved in THF (1 mL) and lithium borohydride (0.10 g, 7.5 eq) was added in three portions. The reaction mixture stirred at rt for 48 h then quenched with saturated ammonium chloride under ice-cooling. The aqueous phase was extracted with DCM and the combined organic phases dried over sodium sulfate and evaporated to afford tert-butyl 4-(3-(hydroxymethyl)phenyl)piperazine-1-carboxylate (0.16 mg, 0.54 mmol, 90%).

Workup

  1. customthen quenched with saturated ammonium chloride under ice-
  2. temperaturecooling
  3. extractionThe aqueous phase was extracted with DCM
  4. dry with materialthe combined organic phases dried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-93e4fd56107549b5b07875aba17556c9
Source dataset
uspto-grants-2016_01
Patent number
US09242987B2

Reaction notes

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