Potassium Carbonate → Tert-butyl (3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate

HRID 1507216노트

반응식

HRID 1507216 반응식
C(OC([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][C@H:16]2[OH:28])=[CH:11][CH:10]=1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:28][C@H:16]1[C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1

참가 물질

4

반응물 2

HCID 11430Potassium CarbonateHCID 118207358HCID 118207358, 화합물

생성물 1

HCID 24820608Tert-butyl (3S,4S)-3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate수율 92%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (±)-rel-(3S,4S)-tert-butyl 4-(4-(tert-butoxycarbonyloxy)phenyl)-3-hydroxypiperidine-1-carboxylate (6.5 g, 16.5 mmol) in 100 mL of methanol was added 11.42 g of potassium carbonate (83 mmol) and the reaction mixture was stirred at rt for 5 h. The organic solvent was removed under reduced pressure and the residue was partitioned between 1N HCl (300 mL) and ethyl acetate (300 mL). The layers were separated and the organic layer was dried over Na2SO4 and evaporated under reduced pressure to give (±)-rel-(3S,4S)-tert-butyl 3-hydroxy-4-(4-hydroxyphenyl)piperidine-1-carboxylate (5 g, 15 mmol, 92% yield) which was used without further purification. LCMS (method F) RT 1.85 min, m/z 238 (M+H+−t-butyl), 279 (M+H+−t-butyl+CH3CN), 1H NMR (400 MHz, DMSO-d6) δ ppm 7.01 (d, J=8.53 Hz, 2H) 6.66 (d, J=8.53 Hz, 2H) 4.70 (d, J=5.02 Hz, 1H) 4.09 (br. s., 1H) 3.94 (d, J=11.55 Hz, 1H) 3.35-3.41 (m, 1H) 2.66-2.77 (m, 1H) 2.29-2.39 (m, 1H) 1.63 (dd, J=13.30, 3.26 Hz, 1H) 1.44-1.52 (m, 1H) 1.42 (s, 9H).

후처리

  1. customThe organic solvent was removed under reduced pressure
  2. customthe residue was partitioned between 1N HCl (300 mL) and ethyl acetate (300 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over Na2SO4
  5. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-1bcfed1c83d14108a01aa6cb21705415
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221796B2

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