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

HRID 1856001Notes

Reaction equation

HRID 1856001 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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).

Workup

  1. dissolution, 79, 189 (1957)] is dissolved in 65 ml
  2. additiontreated with 0.65 ml
  3. customThe bulk of solvent is removed on a rotary evaporator
  4. washof ether and washed with 35 ml
  5. extractionThe wash is back extracted with 35 ml
  6. dry with materialThe combined organic layers are dried (MgSO4)
  7. customthe ether is evaporated
  8. customto give 6.5 g

Sources & evidence

ORD record
ord-94452f71e44043e1834742823590ece0
Source dataset
uspto-grants-1980_08
Patent number
US04217359

Reaction notes

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