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

HRID 1414071ノート

反応式

HRID 1414071 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-a62aaeda397f4eccb37cc322885da3ea
出典データセット
uspto-grants-1981_02
特許番号
US04252943

反応ノート

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