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

HRID 708596ノート

反応式

HRID 708596 の反応式
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]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 75445982HCID 75445982、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-76332f5d97b54634b6b57dbe8bfd3a0b
出典データセット
uspto-grants-2015_11
特許番号
US09175003B2

反応ノート

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