Methyl 4-Boc-piperazine-2-acetate → tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate

HRID 1501969Notes

Reaction equation

HRID 1501969 reaction equation
C[O:2][C:3](=O)[CH2:4][CH:5]1[NH:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:2][CH2:3][CH2:4][CH:5]1[NH:10][CH2:9][CH2:8][N:7]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:6]1

Participants

4

Reactant 2

HCID 2756816Methyl 4-Boc-piperazine-2-acetateHCID 21226445Aluminium lithium hydride

Product 1

HCID 53407692tert-Butyl 3-(2-hydroxyethyl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 3-(2-methoxy-2-oxoethyl)piperazine-1-carboxylate (7.28 g, 28.2 mmol) was dissolved in THF (100 mL) at 0° C. then added LAH (21.14 mL, 21.14 mmol). The reaction was monitored by TLC. After 30 mins, the reaction was first quenched with 0.8 mL water, then added 1.6 mL 2N NaOH followed by 4 mL water. The above slurry was diluted with ethyl acetate and MgSO4 was added. The mixture was stirred at RT for ½ h, then filtered and concentrated to yield the title compound: LC-MS (IE, m/z): 231 [M+1]+.

Workup

  1. customthe reaction was first quenched with 0.8 mL water
  2. additionadded 1.6 mL 2N NaOH
  3. additionThe above slurry was diluted with ethyl acetate and MgSO4
  4. additionwas added
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-aca4e0beef5d48bf9a254e83cabf69ed
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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