Triethylamine → (S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester

HRID 440095

반응식

HRID 440095 반응식
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C>CS(C)=O.C[C@@H]1[C@@H]2C(=C(O)[C@]3(O)C(=O)C(C(N)=O)=C(O)[C@@H](N(C)C)[C@@H]3[C@H]2O)C(=O)C2C(O)=CC=CC1=2.OP(=O)=O.OP(=O)=O.OP(=O)=O.[O-]P(=O)=O.[Na+]>[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH:13]=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

참가 물질

5

반응물 2

HCID 8471TriethylamineHCID 11096562Cbz-L-Prolinol

생성물 1

HCID 11746545(S)-2-Formyl-pyrrolidine-1-carboxylic acid benzyl ester수율 70%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 178461157HCID 178461157, 화합물용매

실험 절차

To a stirred solution of N-Cbz-L-prolinol (5g, 21.26 mmol, from steps 24b or 24c above) in 20 mL of anhydrous DMSO were added 8.89 mL (63.79 mmol) of triethylamine and 10.75 g (63.79 mmol) of SO3 -pyridine complex in 35 mL of DMSC). The reaction mixture was stirred at room temperature for 10 min, then poured into 200 mL of ice water. The mixture was extracted with ether, the extract was dried over Na2SO4 and concentrated to afford the title product, 3.058 g (70% yield).

후처리

  1. extractionThe mixture was extracted with ether
  2. dry with materialthe extract was dried over Na2SO4
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6be8340291294a508f77f2e7a867908c
출처 데이터셋
uspto-grants-1996_05
특허 번호
US05516912

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