Triphenylphosphine → Tert-butyl 4-(2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

HRID 561187

반응식

HRID 561187 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.O[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]([F:25])([F:24])[F:23].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[F:23][C:22]([F:25])([F:24])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[O:1][CH:2]1[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 679582-TrifluoromethylphenolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 643502Tert-butyl 4-hydroxypiperidine-1-carboxylate

생성물 1

HCID 46941590Tert-butyl 4-(2-(trifluoromethyl)phenoxy)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 4-hydroxypiperidine-1-carboxylate (25 g, 124 mmol), 2-hydroxy-benzotrifluoride (22 g, 136 mmol) and triphenylphosphine (39 g, 149 mmol) in THF was added diethyl azodicarboxylate (23.5 mL, 149 mmol) dropwise at 0° C. The mixture was then warmed to room temperature and stirred for 14 h. The mixture was concentrated and diluted with Et2O, washed with 1 N NaOH and water and then dried over Na2SO4. The mixture was concentrated and diluted with Et2O/hexanes (35:65). The precipitated phosphine oxide was filtered and the filtrate was concentrated. The residue was purified by column chromatography on silica gel (eluting with 35% Et2O/hexanes) to give tert-butyl 4-[2-(trifluoromethyl)phenoxy]-piperidine-1-carboxylate as a solid.

후처리

  1. concentrationThe mixture was concentrated
  2. additiondiluted with Et2O
  3. washwashed with 1 N NaOH and water
  4. dry with materialdried over Na2SO4
  5. concentrationThe mixture was concentrated
  6. additiondiluted with Et2O/hexanes (35:65)
  7. filtrationThe precipitated phosphine oxide was filtered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by column chromatography on silica gel (eluting with 35% Et2O/hexanes)

출처 및 근거

ORD 기록
ord-22d4009b29a4441e9cef57dbc9ec5a72
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08063224B2

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