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

HRID 633895ノート

反応式

HRID 633895 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-0005972edaeb4493a6f4060ebaa6b42f
出典データセット
uspto-grants-2016_04
特許番号
US09321769B2

反応ノート

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