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

HRID 59884

반응식

HRID 59884 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-84c2c17968264ec79a61826a50901a96
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440949B2

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