Acetic Acid → Tert-butyl 4-(2-(((trans)-2-phenylcyclopropyl)amino)ethyl)piperidine-1-carboxylate

HRID 529349

반응식

HRID 529349 반응식
O=[CH:2][CH2:3][CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[C:17]1([C@@H:23]2[CH2:25][C@H:24]2[NH2:26])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[C:17]1([C@@H:23]2[CH2:25][C@H:24]2[NH:26][CH2:2][CH2:3][CH:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 19493(1R,2S)-TranylcypromineHCID 5003444Sodium cyanoborohydrideHCID 10353694tert-Butyl 4-(2-oxoethyl)piperidine-1-carboxylate

생성물 1

HCID 68385104Tert-butyl 4-(2-(((trans)-2-phenylcyclopropyl)amino)ethyl)piperidine-1-carboxylate수율 47.5%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of tert-butyl 4-(2-oxoethyl)piperidine-1-carboxylate (1 g, 4.40 mmol) in methanol (15 mL) were added (trans)-2-phenylcyclopropanamine (0.762 g, 5.72 mmol) and acetic acid (0.252 mL, 4.40 mmol), and the mixture was stirred at room temperature for 1 h. Sodium cyanoborohydride (0.415 g, 6.60 mmol) was added and the mixture was stirred at room temperature for 18 h. The reaction was quenched with water (10 mL) and the mixture was concentrated to remove methanol. The resulting aqueous layer was extracted with DCM (3×). The DCM extract was washed with 10% HOAc aqueous solution, dried (Na2SO4) and concentrated. The residue was purified using column chromatography (silica gel, 0 to 100% EtOAc/hexanes) to give 720 mg of product as pale yellow oil. MS: (M+H)+=345.4. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.94-1.75 (m, 18H), 1.86-1.95 (m, 1H), 2.35 (dt, J=7.01, 3.69 Hz, 1H), 2.60-2.86 (m, 4H), 4.08 (br. s., 2H), 6.91-7.38 (m, 5H).

후처리

  1. stirringthe mixture was stirred at room temperature for 18 h
  2. customThe reaction was quenched with water (10 mL)
  3. concentrationthe mixture was concentrated
  4. customto remove methanol
  5. extractionThe resulting aqueous layer was extracted with DCM (3×)
  6. extractionThe DCM extract
  7. washwas washed with 10% HOAc aqueous solution
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue was purified

출처 및 근거

ORD 기록
ord-b57e33a5fbd843d781b00fad57cdb135
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346840B2

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