Aluminium lithium hydride → HCID 57420366, compound

HRID 2403429Notes

Reaction equation

HRID 2403429 reaction equation
C[O:2][C:3]([CH:5]1[N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[CH2:9][CH2:8][N:7]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:18]([O:17][C:15]([N:7]1[CH2:8][CH2:9][N:10]([S:11]([CH3:14])(=[O:13])=[O:12])[CH:5]([CH2:3][OH:2])[CH2:6]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57494066HCID 57494066, compound

Product 1

HCID 57420366HCID 57420366, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester (8.4 g, crude) in DMF (50 mL) was added K2CO3 (7.5 g) and iodomethane (8.5 mL) The mixture was stirred overnight at R.T. An aqueous work-up followed by purification on silica gave 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (3.267 g). A solution of 4-methanesulfonyl-piperazine-1,3-dicarboxylic acid 1-tert-butyl ester 3-methyl ester (3.2 g) in dry THF (20 mL) was added via cannular to a mixture of lithium aluminium hydride (0.75 g) in THF (30 mL) at 0° C. and under N2 atmosphere. The resultant mixture was then warmed to R.T. and stirred for 2.5 h. The reaction was carefully quenched with aqueous ammonium chloride (5 mL) then filtered over Celite. An aqueous work-up followed by purification on silica gave 3-hydroxymethyl-4-methanesulfonyl-piperazine-1-carboxylic acid tert-butyl ester (1.13 g).

Workup

  1. customThe reaction was carefully quenched with aqueous ammonium chloride (5 mL)
  2. filtrationthen filtered over Celite
  3. customAn aqueous work-up followed by purification on silica

Sources & evidence

ORD record
ord-8cbc14dcbdb943c7aa1cc0340df44bce
Source dataset
uspto-grants-2014_08
Patent number
US08802670B2

Reaction notes

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