Potassium Carbonate → tert-Butyl 3-ethynylpiperidine-1-carboxylate

HRID 535861

반응식

HRID 535861 반응식
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([CH:14]=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:16]OP(C=[N+]=[N-])(=O)OC.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH:10]([C:14]#[CH:16])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5115033Dimethyl (diazomethyl)phosphonateHCID 99644481-Boc-piperidine-3-carboxaldehyde

생성물 1

HCID 21963855tert-Butyl 3-ethynylpiperidine-1-carboxylate수율 100.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

A solution of 1-BOC-3-formylpiperidine (1.46 g, 6.85 mmol) and (diazomethyl) phosphonic acid dimethyl ester (1.79 g, 11.94 mmol) in 50 mL methanol was stirred at ice-bath for 10 min, K2CO3 (1.96 g, 14.2 mmol) was added to the above mixture and stirred at ice-bath for 2 hrs, then stirred at rt overnight. The mixture was evaporated in vacuo, to the residue was added EtOAc and water, the organic layer was separated and water layer was extracted with EtOAc (100 mL×3). The combined organic layers were washed with water and brine successively, dried with Na2SO4, filtered, and the filtrate was evaporated in vacuo to give 1.44 g product as colorless oil (100.0%). 1H NMR (300 MHz, CDCl3) δ: 3.90 (1H, brs), 3.70-3.75 (1H, m), 2.95-3.02 (2H, m), 2.40-2.47 (1H, m), 2.05 (1H, d, J=2.1 Hz), 1.94-1.99 (1H, m), 1.69-1.73 (1H, m), 1.50-1.63 (2H, m), 1.46 (9H, s).

후처리

  1. stirringstirred at rt overnight
  2. customThe mixture was evaporated in vacuo, to the residue
  3. additionwas added EtOAc and water
  4. customthe organic layer was separated
  5. extractionwater layer was extracted with EtOAc (100 mL×3)
  6. washThe combined organic layers were washed with water and brine successively
  7. dry with materialdried with Na2SO4
  8. filtrationfiltered
  9. customthe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-fee5f01557c74cd9a77029b6804140ff
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859553B2

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