Aluminium lithium hydride → 4-(4-Hydroxymethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

HRID 1516510Notes

Reaction equation

HRID 1516510 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[S:15][CH:16]=[C:17]([C:19](OCC)=[O:20])[N:18]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[S:15][CH:16]=[C:17]([CH2:19][OH:20])[N:18]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 53418800Ethyl 2-(4-(tert-butoxycarbonyl)piperazin-1-YL)thiazole-4-carboxylate

Product 1

HCID 574237984-(4-Hydroxymethyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-(4-ethoxycarbonyl-thiazol-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (1.15 g, 3.37 mmol) in THF (15 mL) at 0° C. was treated with LiAlH4 (128 mg, 1 eq.). The mixture was stirred for 1 hour, then the reaction was quenched with 2 N NaOH solution. The solid was filtered off through a pad of celite and washed with EtOAc (100 mL). The filtrate was washed with water and dried over Na2SO4. Removal of the solvent afforded the desired product as an oil.

Workup

  1. customthe reaction was quenched with 2 N NaOH solution
  2. filtrationThe solid was filtered off through a pad of celite
  3. washwashed with EtOAc (100 mL)
  4. washThe filtrate was washed with water
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent

Sources & evidence

ORD record
ord-987762f2b53b4c71a2ea803a310409e5
Source dataset
uspto-grants-2012_07
Patent number
US08227495B2

Reaction notes

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