Isopropyl 4-Hydroxypiperidine-1-carboxylate → HCID 86597364、化合物

HRID 1036793ノート

反応式

HRID 1036793 の反応式
Cl[C:2]1[C:7]([CH2:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=1.[CH:11]([O:14][C:15]([N:17]1[CH2:22][CH2:21][CH:20]([OH:23])[CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].CC(C)([O-])C.[K+]>C1COCC1>[CH:11]([O:14][C:15]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][C:2]2[C:7]([CH2:8][CH3:9])=[C:6]([Cl:10])[N:5]=[CH:4][N:3]=2)[CH2:21][CH2:22]1)=[O:16])([CH3:13])[CH3:12]

参加物

5

反応物 3

HCID 16745126Isopropyl 4-Hydroxypiperidine-1-carboxylateHCID 218284324,6-Dichloro-5-ethylpyrimidineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 86597364HCID 86597364、化合物収率 40%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4,6-dichloro-5-ethyl-pyrimidine (1 g, 5.65 mmol) and 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (1.05 g, 5.65 mmol) in dry THF under nitrogen at 0° C., potassium tert-butoxide (1M solution in THF, 6.78 mL) was added dropwise. The reaction was stirred at rt for 30 min. The mixture was quenched with water and extracted with EtOAc (3×). The organic layer was washed with water, sat. NH4Cl and brine, followed by drying over sodium sulfate and concentration under vacuo. The resulting oil was purified by HPLC to afford 4-(6-chloro-5-ethyl-pyrimidin-4-yloxy)-piperidine-1-carboxylic acid isopropyl ester (0.74 g, 39.8%) as a colorless oil. Exact mass calculated for C15H22ClN3O3 327.13, found 328.2 (MH+).

後処理

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc (3×)
  3. washThe organic layer was washed with water, sat. NH4Cl and brine
  4. dry with materialby drying over sodium sulfate and concentration under vacuo
  5. customThe resulting oil was purified by HPLC

出典と根拠

ORDレコード
ord-e2789ecc7188474b801163ef269f9a81
出典データセット
uspto-grants-2013_10
特許番号
US08546429B2

反応ノート

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