Triphenylphosphine → N-(3-{1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

HRID 1832173노트

반응식

HRID 1832173 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[OH:32][C@H:33]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH:39]([C:42]2[CH:43]=[C:44]([NH:48][C:49](=[O:53])[CH:50]([CH3:52])[CH3:51])[CH:45]=[CH:46][CH:47]=2)[CH2:38][CH2:37]1.[CH3:60][O:61][C:62]1[CH:63]=[C:64](O)[CH:65]=[CH:66][C:67]=1[O:68][CH3:69]>C1COCC1>[CH3:60][O:61][C:62]1[CH:63]=[C:64]([CH:65]=[CH:66][C:67]=1[O:68][CH3:69])[O:32][C@@H:33]([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[CH2:34][CH2:35][N:36]1[CH2:41][CH2:40][CH:39]([C:42]2[CH:43]=[C:44]([NH:48][C:49](=[O:53])[CH:50]([CH3:52])[CH3:51])[CH:45]=[CH:46][CH:47]=2)[CH2:38][CH2:37]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 162513,4-DimethoxyphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 60078700N-(3-{1-[(3S)-3-Hydroxy-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide

생성물 1

HCID 10279479N-(3-{1-[(3R)-3-(3,4-Dimethoxyphenoxy)-3-Phenylpropyl]-4-Piperidinyl}Phenyl)-2-Methylpropanamide수율 34.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Into a 25-mL RB-flask was added triphenylphosphine (9.80 mg, 0.0375 mmol), diethyl azodicarboxylate (5.22 mg, 0.0300 mmol), N-(3-{1-[(3S)-3-hydroxy-3-phenylpropyl]-4-piperidinyl}phenyl)-2-methylpropanamide (9.53 mg, 0.0250 mmol), 3,4-dimethoxyphenol (7.70 mg, 0.050 mmol) and THF (1.0 mL) at room temperature. The reaction mixture was stirred at room temperature overnight (16 hrs). The solvent was removed under reduced pressure and the residue was purified by preparative TLC plates [2.5% of NH3 (2.0 M in methanol) in CHCl3] to afford the desired product (4.4 mg, 34.1% yield) as a thick oil: 1H NMR (400 MHz, CDCl3) δ7.46 (s, 1H), 7.40–7.30 (m, 4H) 7.25 (m, 3H), 6.97 (d, 1H, J=7.8 Hz), 6.64 (d, 1H, J=9.1 Hz), 6.51 (d, 1H, J=2.6 Hz), 6.29 (d, 1H, J=2.6, 9.1 Hz), 5.20 (apparent dd, 1H, J=4.4, 8.5 Hz), 3.80 (s, 3H), 3.77 (s, 3H), 3.23 (m, 2H), 2.77 (m, 2H), 2.5 (m, 2H), 2.3–2.1 (m, 6H), 1.80 (m, 2H), 1.25 (d, 6H, J=7.9 Hz); ESMS m/e: 517.4 (M+H)+.

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative TLC plates [2.5% of NH3 (2.0 M in methanol) in CHCl3]

출처 및 근거

ORD 기록
ord-487d3c4481bb42f4a67e224db4c58c5b
출처 데이터셋
uspto-grants-2006_06
특허 번호
US07067534B1

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