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

HRID 1888078노트

반응식

HRID 1888078 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-effb230ba5484bcf830d4558f96835dd
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501773B2

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