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

HRID 1507216ノート

反応式

HRID 1507216 の反応式
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

参加物

4

反応物 2

HCID 11430Potassium CarbonateHCID 118207358HCID 118207358、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1bcfed1c83d14108a01aa6cb21705415
出典データセット
uspto-grants-2015_12
特許番号
US09221796B2

反応ノート

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