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

HRID 577275Notes

Reaction equation

HRID 577275 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-bb90e575d8874a27b8e5373e94d6bc73
Source dataset
uspto-grants-2015_05
Patent number
US09040545B2

Reaction notes

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