Water → HCID 67277658, compound

HRID 1695702Notes

Reaction equation

HRID 1695702 reaction equation
C([O:3][C:4]([CH:6]1[CH2:11][N:10]([S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:9][CH:8]([C:21](OCC)=[O:22])[N:7]1[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:15]1([S:12]([N:10]2[CH2:11][CH:6]([CH2:4][OH:3])[N:7]([CH2:26][C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:8]([CH2:21][OH:22])[CH2:9]2)(=[O:14])=[O:13])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 67278285HCID 67278285, compound

Product 1

HCID 67277658HCID 67277658, compoundYield 78.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of the above described (2SR,6SR)-4-benzenesulfonyl-1-benzyl-piperazine-2,6-dicarboxylic acid diethyl ester (7.0 g, 15 mmol) in tetrahydrofuran (165 ml) at 23° C. was added a solution of lithium aluminum hydride in tetrahydrofuran (c=1 mol/l, 45.6 ml, 45.6 mmol) and the mixture was stirred at 70° C. for 1 h. Then the reaction was cooled to 0° C., water (1.75 ml) was added very slowly, then NaOH 15% (1.75 ml) and water (5.24 ml). The mixture was stirred at 23° C. for 1.5 h, the precipitate was filtered off, washed with tetrahydrofuran and the organic layer was evaporated totally to give the title compound as a white solid (4.45 g, 78%), MS (ISP) m/e=377.3 [(M+H)+].

Workup

  1. customat 23° C.
  2. temperatureThen the reaction was cooled to 0° C.
  3. stirringThe mixture was stirred at 23° C. for 1.5 h
  4. filtrationthe precipitate was filtered off
  5. washwashed with tetrahydrofuran
  6. customthe organic layer was evaporated totally

Sources & evidence

ORD record
ord-7f04baa0414942878cb42f49279aae44
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

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