Borane → tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

HRID 1888078ノート

反応式

HRID 1888078 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:15]#[N:16])([F:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[NH2:16][CH2:15][C:11]1([F:14])[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:2])[CH3:4])=[O:7])[CH2:13][CH2:12]1

参加物

4

反応物 2

HCID 6331BoraneHCID 46242032Tert-butyl 4-cyano-4-fluoropiperidine-1-carboxylate

生成物 1

HCID 40152119tert-Butyl 4-aminomethyl-4-fluoropiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a 0° C. solution of 4-3 (8.83 g, 38.7 mmol) in 75 mL dry THF was added a solution of 1 M borane in THF (155 mL, 155 mmol) over 30 min. After 30 min more, the cold reaction was slowly quenched with EtOH (200 mL) and all solvent was removed in vacuo. The residue was taken up in saturated aq. NH4Cl/EtOAc (150 mL) and extracted with EtOAc (3×150 mL). The organic layers were washed with 1 N aq. NaOH, brine, dried over MgSO4, filtered, and concentrated in vacuo, giving crude 4-4 as a pale yellow oil. The crude amine 4-4 was carried forward. 1H NMR (CDCl3, 300 MHz): 3.94 (br, 2H), 3.08 (m, 2H), 1.85 (m, 2H), 1.51 (m, 4H), 1.44 (s, 9H); MS (Electrospray): m/z 218.2 (M−Me+H), 177.2 (M−t−Bu+H).

後処理

  1. customthe cold reaction
  2. customwas slowly quenched with EtOH (200 mL)
  3. customall solvent was removed in vacuo
  4. extractionextracted with EtOAc (3×150 mL)
  5. washThe organic layers were washed with 1 N aq. NaOH, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-effb230ba5484bcf830d4558f96835dd
出典データセット
uspto-grants-2013_08
特許番号
US08501773B2

反応ノート

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