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

HRID 1638401노트

반응식

HRID 1638401 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9342c11d70c541e3894086d32d0d2bb1
출처 데이터셋
uspto-grants-1989_11
특허 번호
US04879392

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