Formaldehyde → Dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylate

HRID 478776

반응식

HRID 478776 반응식
[CH2:1]([NH:8][CH2:9]C(O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:13]([O:21][CH3:22])(=[O:20])/[CH:14]=[CH:15]\[C:16]([O:18][CH3:19])=[O:17].C=O.[CH3:25]CN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[CH2:1]([N:8]1[CH2:9][C@H:15]([C:16]([O:18][CH3:19])=[O:17])[C@H:14]([C:13]([O:21][CH3:22])=[O:20])[CH2:25]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 712FormaldehydeHCID 81531DiisopropylethylamineHCID 869652-(Benzylamino)acetic acidHCID 5271565Dimethyl maleate

생성물 1

HCID 10978757Dimethyl (3R,4S)-1-benzylpyrrolidine-3,4-dicarboxylate수율 34.6%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of N-benzylglycine (12.39 g, 75 mmol), dimethyl maleate (6.26 g, 50 mmol), paraformaldehyde (4.5 g, 150 mmol) and DIEA (8.7 mL, 50 mmol) in toluene (100 mL) was stirred at reflux for 2 hours and concentrated. The residue was taken up in EtOAc. The solution was washed with brine 3×, dried (MgSO4) and concentrated. Column chromatography eluting with 50% EtOAc/hexanes provided dimethyl cis-1-benzyl-3,4-pyrrolidinedicarboxylate (4.8 g, 34%). MS (M+H)+=278.5.

후처리

  1. temperatureat reflux for 2 hours
  2. concentrationconcentrated
  3. washThe solution was washed with brine 3×
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. washColumn chromatography eluting with 50% EtOAc/hexanes

출처 및 근거

ORD 기록
ord-46dd9d23806947f28dc42014a3fe4a85
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06642255B2

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