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

HRID 535861

反応式

HRID 535861 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 21963855tert-Butyl 3-ethynylpiperidine-1-carboxylate収率 100.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fee5f01557c74cd9a77029b6804140ff
出典データセット
uspto-grants-2014_10
特許番号
US08859553B2

関連ノート

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