Lithium Hydroxide → HCID 20437871, compound

HRID 1980038Notes

Reaction equation

HRID 1980038 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([O:17]C)=[O:16])[C:10](=[O:19])[CH:9]1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]([OH:17])=[O:16])[C:10](=[O:19])[CH:9]1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:25][CH:26]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 12638305HCID 12638305, compound

Product 1

HCID 20437871HCID 20437871, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

t-Boc-piperazinoneacetate 4a (0.251 g, 5.37×10-4 mole), 1M aqueous LiOH (0.59 ml, 5.9×10-4 mole), and methanol (2 ml) are stirred at room temperature for 2 hours. The solvent is then evaporated and the resulting yellow oil is dissolved in CH2Cl2 and transferred to a separatory funnel where it is washed with 0.5M aqueous HCl. The CH2Cl2 layer is separated and the acidic aqueous phase is extracted with CH2Cl2 (3 times). The CH2Cl2 extracts are combined and washed with saturated aqueous NaCl before being dried over Na2SO4. Filtration of the drying agent and evaporation of the filtrate gives 5a as a colorless foam, which was shown to be homogeneous by TLC on silica gel plates. The structure of 5a was corroborated by NMR. NMR (CDCl3) δ 1.27 (S, 9, t-boc), 3.09-4.07 (m, 8, methylenes), 4.68 (t, 1, C3 -H), 4.97 (S, 2, benzyloxy methylene), 6.89 (q, 4, aromatic), 7.30 (S, 5, aromatic), 9.99 (broad S, 1, acid).

Workup

  1. customThe solvent is then evaporated
  2. dissolutionthe resulting yellow oil is dissolved in CH2Cl2
  3. customtransferred to a separatory funnel
  4. washwhere it is washed with 0.5M aqueous HCl
  5. customThe CH2Cl2 layer is separated
  6. extractionthe acidic aqueous phase is extracted with CH2Cl2 (3 times)
  7. washwashed with saturated aqueous NaCl
  8. dry with materialbefore being dried over Na2SO4
  9. filtrationFiltration of the drying agent and evaporation of the filtrate

Sources & evidence

ORD record
ord-daf18b923fb84a8ebf1f9f81c7fea319
Source dataset
uspto-grants-1984_11
Patent number
US04483988

Reaction notes

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