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

HRID 708596Notes

Reaction equation

HRID 708596 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 dired 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

Sources & evidence

ORD record
ord-76332f5d97b54634b6b57dbe8bfd3a0b
Source dataset
uspto-grants-2015_11
Patent number
US09175003B2

Reaction notes

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