Phenol → Tert-butyl 3-phenoxypyrrolidine-1-carboxylate

HRID 82922ノート

反応式

HRID 82922 の反応式
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH:28]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29]1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:7]([CH:32]1[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:31]1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 44169391-Boc-3-pyrrolidinolHCID 5462977Diethyl azodicarboxylate

生成物 1

HCID 23512104Tert-butyl 3-phenoxypyrrolidine-1-carboxylate収率 25%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Phenol (503 mg, 5.34 mmol) and triphenylphosphine (1.40 g, 5.34 mmol) were added to a solution of tert-butyl 3-hydroxypyrrolidine-1-carboxylate (500 mg, 2.67 mmol; which may be prepared as described in Step 1) in anhydrous THF (13 mL) under nitrogen. 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 and brine, dried over Na2SO4 then concentrated. The residue was purified on column chromatography (eluent: pentane EtOAc 9/1) to give the title compound (175 mg, 25%) as a yellow oil.

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 and brine
  6. dry with materialdried over Na2SO4
  7. concentrationthen concentrated
  8. customThe residue was purified on column chromatography (eluent: pentane EtOAc 9/1)

出典と根拠

ORDレコード
ord-4be5dd4fbdd14578b498b174b584f8c4
出典データセット
uspto-grants-2014_09
特許番号
US08846711B2

反応ノート

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