Aluminium lithium hydride → 3-Aminomethyl-5-fluoromethylbenzylalcohol

HRID 473239노트

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HRID 473239 반응식
[N:1]([CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][F:16])[CH:14]=1)[C:8](OC)=[O:9])=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([CH2:15][F:16])[CH:14]=1)[CH2:8][OH:9]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86671517Methyl 3-azidomethyl-5-fluoromethylbenzoate2회

생성물 1

HCID 672534013-Aminomethyl-5-fluoromethylbenzylalcohol수율 48%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

Methyl 3-azidomethyl-5-fluoromethylbenzoate (35) (476 mg, 2.13 mmol) was dissolved in THF (21.3 mL). The air was evacuated from the reaction system, and then Ar was charged therein. In another recovery flask filled with Ar, LiAlH4 (408 mg, 10.7 mmol) was placed. To this was added THF (21.3 mL) with ice-cooling to give a suspension. To the suspension was added dropwise the solution of the compound (35), and stirred for 2 hours at 0° C. TLC was used to confirm there was no starting material in the mixture. Then, the reaction was quenched with MeOH (10 mL). The mixture was filtered through cerite to remove metals. The filtrate was evaporated under reduced pressure. The residue was purified by neutral silica gel column chromatography (hexane:EtOAc=1:1, then EtOAc:MeOH=2:1) to isolate 3-aminomethyl-5-fluoromethylbenzylalcohol (38) (172 mg, 48%) as a yellow solid.

후처리

  1. customThe air was evacuated from the reaction system
  2. additionAr was charged
  3. temperaturecooling
  4. customto give a suspension
  5. customThen, the reaction was quenched with MeOH (10 mL)
  6. filtrationThe mixture was filtered through cerite
  7. customto remove metals
  8. customThe filtrate was evaporated under reduced pressure
  9. customThe residue was purified by neutral silica gel column chromatography (hexane

출처 및 근거

ORD 기록
ord-4dfb9da26e904d4fb5444bc8adfc1575
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633304B2

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