Triphenylphosphine → HCID 86614210, 화합물

HRID 888090노트

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HRID 888090 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]([OH:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30]O)=[O:24])([CH3:21])([CH3:20])[CH3:19].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[C:18]([O:22][C:23]([N:25]1[CH2:29][CH2:28][CH2:27][C@H:26]1[CH2:30][O:17][C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=1)([C:9]([F:10])([F:11])[F:12])[C:13]([F:14])([F:15])[F:16])=[O:24])([CH3:21])([CH3:19])[CH3:20]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 643448(S)-(-)-N-Boc-prolinolHCID 5462977Diethyl azodicarboxylateHCID 133206092-(3-Aminophenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol

생성물 1

HCID 86614210HCID 86614210, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 2-(3-amino-phenyl)-1,1,1,3,3,3-hexafluoro-propan-2-ol (1.30 g), (S)-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (1.04 g), PPh3 (2.64 g) and molecular sieves 4 Å in THF (100 mL) was added DEAD (1.55 mL) slowly. The reaction was stirred at RT for 4 h and at reflux for overnight. After filtration to remove solids, the filtrate was concentrated and the residue was taken into Et2O. The organic phase was washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and evaporated to give a crude compound as very viscous brown oil, which was purified by chromatography through silica gel (500 g, 30% to 50% EtOAc in hexanes) to afford (S)-2-[1-(3-amino-phenyl)-2,2,2-trifluoro-1-trifluoromethyl-ethoxymethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester as a light brown oil.

후처리

  1. temperatureat reflux for overnight
  2. filtrationAfter filtration
  3. customto remove solids
  4. concentrationthe filtrate was concentrated
  5. washThe organic phase was washed with saturated NaHCO3 and brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. customevaporated
  8. customto give a crude compound as very viscous brown oil, which
  9. customwas purified by chromatography through silica gel (500 g, 30% to 50% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-fc99ffb73d7742f98234fecb34d9455b
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247556B2

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