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

HRID 708596노트

반응식

HRID 708596 반응식
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]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 75445982HCID 75445982, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-76332f5d97b54634b6b57dbe8bfd3a0b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175003B2

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