Pyrrolidine → (1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine

HRID 1638401Notes

Reaction equation

HRID 1638401 reaction equation
[C:1]1(=[O:10])[C@H:9]2[C@H:4]([CH2:5][CH2:6][CH2:7][CH2:8]2)[CH2:3][O:2]1.C[O-].[Na+].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>CO>[OH:2][CH2:3][C@H:4]1[CH2:5][CH2:6][CH2:7][CH2:8][C@@H:9]1[C:1]([N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:10]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 10942334Sodium MethoxideHCID 11126340cis-hexahydroisobenzofuran-1(3H)-one

Product 1

HCID 14127584(1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4 g of (3aS,cis) hexahydro-1-(3H)-isobenzofuranone in 20 ml of methanol and 4.76 ml of pyrrolidine with 0.386 g of sodium methylate were refluxed for 20 hours and one half of the methanol was distilled off at 50° C. under reduced pressure. Water and ice were added and the pH was adjusted to 1 by adding 2N hydrochloric acid. Extraction was done with methylene chloride and the extracts were washed with water, dried, filtered, evaporated to dryness under reduced pressure and crystallized from isopropyl ether to obtain 3.89 g of (1S,trans) 1-[(2hydroxymethyl-1-cyclohexyl)-carbonyl]-pyrrolidine melting at 115° C.

Workup

  1. distillationone half of the methanol was distilled off at 50° C. under reduced pressure
  2. additionWater and ice were added
  3. additionby adding 2N hydrochloric acid
  4. extractionExtraction
  5. washthe extracts were washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated to dryness under reduced pressure
  9. customcrystallized from isopropyl ether

Sources & evidence

ORD record
ord-9342c11d70c541e3894086d32d0d2bb1
Source dataset
uspto-grants-1989_11
Patent number
US04879392

Reaction notes

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