Tetrahydrofuran → HCID 18328912, compound

HRID 1249730Notes

Reaction equation

HRID 1249730 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14](C(OCC)=O)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+].[O:24]1CCCC1>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][N:14]([OH:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 4148881Lithium borohydrideHCID 18328919HCID 18328919, compound

Product 1

HCID 18328912HCID 18328912, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of oil 1-benzyloxycarbonyl-4-ethoxycarbonyl-piperazine (30 g) in tetrahydrofuran (200 ml) was added lithiumborohydride (2.7 g) and stirred at 60° C. for 5 hours. To quench thc mixture, added methanol, dilute hydrochloric acid and then concentrated hydrochloric acid. Diluted with diethylether and resulting suspension washed with water (×2) dilute sodiumbicarbonate then brine, dried (MgSO4) and evaporated to give as a colourless oil oil 1-benzyloxycarbonyl-4-hydroxy-piperazine (23 g) which was used directly in the next step without further purification or characterisation.

Workup

  1. customTo quench thc mixture
  2. additionadded methanol, dilute hydrochloric acid
  3. additionDiluted with diethylether
  4. customresulting suspension
  5. washwashed with water (×2) dilute sodiumbicarbonate
  6. dry with materialbrine, dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-39c7c9664aa64fceb533af7f390ecc0f
Source dataset
uspto-grants-2002_01
Patent number
US06335341B1

Reaction notes

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