Methanol → (2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

HRID 1414071

반응식

HRID 1414071 반응식
[C:1]([N:11]1[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:20]O.S(=O)(=O)(O)O>C(Cl)(Cl)Cl>[C:1]([N:11]1[CH2:18][C@@H:17]([OH:19])[CH2:16][C@H:12]1[C:13]([O:15][CH3:20])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

참가 물질

5

반응물 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 688414(2S,4S)-1-((Benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

생성물 1

HCID 688413(2S,4S)-1-Benzyl 2-methyl 4-hydroxypyrrolidine-1,2-dicarboxylate

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

6.5 g (0.024 mole) of N-carbobenzyloxy-cis-4-hydroxy-L-proline [J.A.C.S., 79, 189 (1957)] is dissolved in 65 ml. of methanol, stirred, and treated with 0.65 ml. of concentrated sulfuric acid. After stirring at room temperature for one-half hour, the solution is allowed to stand overnight. The bulk of solvent is removed on a rotary evaporator and the oily residue (13 g.) is taken up in 70 ml. of ether and washed with 35 ml. of 10% sodium bicarbonate solution. The wash is back extracted with 35 ml. of ether. The combined organic layers are dried (MgSO4), and the ether is evaporated to give 6.5 g. (96%) of product as a pale yellow viscous oil. [α]D25 -24° (c, 1% in chloroform).

후처리

  1. additiontreated with 0.65 ml
  2. customThe bulk of solvent is removed on a rotary evaporator
  3. washof ether and washed with 35 ml
  4. extractionThe wash is back extracted with 35 ml
  5. dry with materialThe combined organic layers are dried (MgSO4)
  6. customthe ether is evaporated
  7. customto give 6.5 g

출처 및 근거

ORD 기록
ord-a62aaeda397f4eccb37cc322885da3ea
출처 데이터셋
uspto-grants-1981_02
특허 번호
US04252943

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