Triphenylphosphine → tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate

HRID 59884ノート

反応式

HRID 59884 の反応式
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[CH3:2].O[C@H:12]1[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C@@H:16]1[CH2:17][CH2:12][CH2:13][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1)[CH3:2]

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 667552-EthoxyphenolHCID 1514399tert-butyl (3S)-3-hydroxypiperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylate

生成物 1

HCID 131737068tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate収率 45.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a solution of 2-ethoxyphenol (13.72 g, 99 mmol), tert-butyl (S)-3-hydroxypiperidine-1-carboxylate (20 g, 99 mmol), and triphenylphosphine (29 g, 111 mmol) in toluene (150 mL) at 20-25° C. was added a solution of DIAD (20 mL, 104 mmol) in toluene (50 mL) over 2 hours. After 2 hours, the reaction mixture was filtered and washed with diethyl ether (300 mL). The filtrate was washed with 3N NaOH (150 mL), dried over Na2SO4, and concentrated. The crude residue was purified via column chromatography to afford tert-butyl (R)-3-(2-ethoxyphenoxy)piperidine-1-carboxylate (14.6 g, 45%). MS (ES+) 222.2 (M-100+H).

後処理

  1. filtrationthe reaction mixture was filtered
  2. washwashed with diethyl ether (300 mL)
  3. washThe filtrate was washed with 3N NaOH (150 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe crude residue was purified via column chromatography

出典と根拠

ORDレコード
ord-84c2c17968264ec79a61826a50901a96
出典データセット
uspto-grants-2016_09
特許番号
US09440949B2

反応ノート

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