Tetrahydrofuran → (+/-)-(4R*,5R*)-5-[(1R*)hydroxy(3-methylphenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one

HRID 1837994노트

반응식

HRID 1837994 반응식
[CH:1]([C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:2].C1COCC1.[C:21]1([CH3:29])[CH:26]=[CH:25][CH:24]=[C:23]([Mg]Cl)[CH:22]=1.[NH4+].[Cl-]>O>[OH:2][C@H:1]([C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([CH3:29])[CH:22]=1)[C@@H:3]1[N:7]([CH3:8])[C:6](=[O:9])[CH2:5][C@@H:4]1[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 13825985(-)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one2회HCID 178425419HCID 178425419, 화합물

생성물 1

HCID 59066530(+/-)-(4R*,5R*)-5-[(1R*)hydroxy(3-methylphenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one수율 77%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a 0° C. solution of (±)-(4R*,5R*)-5-formyl-1-methyl-4-phenylpyrrolidin-2-one (Intermediate Z, 74 mg, 0.4 mmol) in anhyd. THF (5 mL) was added a solution of m-tolyl magnesium chloride (1M in THF, 0.5 mL, 0.5 mmol, 1.25 equiv). The reaction mixture was stirred for 1 h, then treated with a saturated NH4Cl solution and water. The resulting mixture was extracted with EtOAc, dried (Na2SO4) and concentrated under reduced pressure. The residue was triturated (Et2O/hex) to give (±)-(4R*,5R*)-5-[(1R*)hydroxy(3-methylphenyl)methyl]-1-methyl-4-phenylpyrrolidin-2-one (82 mg, 77%): mp 163-165° C.; TLC (EtOAc) Rf 0.45.

후처리

  1. customTo a 0° C.
  2. extractionThe resulting mixture was extracted with EtOAc
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was triturated (Et2O/hex)

출처 및 근거

ORD 기록
ord-83550188104e44c7807d4996595fe7a2
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06784167B2

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