Aluminium lithium hydride → Tert-butyl 5-(hydroxymethyl)-4-methylthiazol-2-ylcarbamate

HRID 879705Notes

Reaction equation

HRID 879705 reaction equation
C[O:2][C:3]([C:5]1[S:9][C:8]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[N:7][C:6]=1[CH3:18])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:14]([O:13][C:11](=[O:12])[NH:10][C:8]1[S:9][C:5]([CH2:3][OH:2])=[C:6]([CH3:18])[N:7]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 75445982HCID 75445982, compound

Product 1

HCID 23560820Tert-butyl 5-(hydroxymethyl)-4-methylthiazol-2-ylcarbamateYield 89.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-tert-Butoxycarbonylamino-4-methyl-thiazole-5-carboxylic acid methyl ester (0.5 g) was dissolved in anhydrous THF (7 mL) and cooled to 0° C. and 1 eq of Lithium aluminum hydride (2M solution in THF) was added and stirred 1 h. Reaction was slowly warmed to RT and stirred for 6 h. Reaction was cooled to 0° C. and quenched with min amount of sat. Na2SO4 soln. White solid was filtered and washed with ethyl acetate (5 mL), filtrate was concentrated by rotavap and residue was dried in vacuum gave (5-Hydroxymethyl-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.4 g). This was used in the next reaction without further purification. 1H NMR (400 MHz, Acetone-d6) 4.6 (s, 2H), 2.1 (s, 3H), 1.5 (s, 9H).

Workup

  1. customReaction
  2. temperaturewas slowly warmed to RT
  3. stirringstirred for 6 h
  4. customReaction
  5. temperaturewas cooled to 0° C.
  6. customquenched with min amount of sat. Na2SO4 soln
  7. filtrationWhite solid was filtered
  8. washwashed with ethyl acetate (5 mL), filtrate
  9. concentrationwas concentrated by rotavap
  10. customresidue was dried in vacuum

Sources & evidence

ORD record
ord-6dbb1bdef62d483fad183e87b192c29d
Source dataset
uspto-grants-2015_03
Patent number
US08987295B2

Reaction notes

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