Aluminium lithium hydride → 3-Aminomethyl-5-fluoromethylbenzylalcohol

HRID 473239ノート

反応式

HRID 473239 の反応式
[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]

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 86671517Methyl 3-azidomethyl-5-fluoromethylbenzoate2 回

生成物 1

HCID 672534013-Aminomethyl-5-fluoromethylbenzylalcohol収率 48%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4dfb9da26e904d4fb5444bc8adfc1575
出典データセット
uspto-grants-2014_01
特許番号
US08633304B2

反応ノート

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