3-Hydroxypyridine → tert-Butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate

HRID 82939노트

반응식

HRID 82939 반응식
[OH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]1.O[C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:1][CH:2]2[CH2:6][CH2:5][N:4]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:3]2)[CH:16]=1

참가 물질

6

반응물 4

HCID 79713-HydroxypyridineHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 10801570tert-Butyl 3-(pyridin-3-yloxy)pyrrolidine-1-carboxylate수율 86%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

To a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol) in anhydrous THF (13 mL) under nitrogen were added 3-hydroxypyridine (508 mg, 5.34 mmol) and triphenylphosphine (1.40 g, 5.34 mmol). The reaction mixture was cooled to 0° C. and DEAD (775 μL, 4.27 mmol) was added dropwise. The solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was concentrated under reduced pressure then diluted with dichloromethane and filtered. The filtrate was washed three times with NaOH 0.2N, dried over Na2SO4 then concentrated. The residue was purified on column chromatography (eluent: pentane/acetone 9/1 to 7/3) to give the title compound (606 mg, 86%) as a wax.

후처리

  1. temperatureto warm to room temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthen diluted with dichloromethane
  4. filtrationfiltered
  5. washThe filtrate was washed three times with NaOH 0.2N
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated
  8. customThe residue was purified on column chromatography (eluent: pentane/acetone 9/1 to 7/3)

출처 및 근거

ORD 기록
ord-ea994b67ad46432c991f54d828155fed
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846711B2

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