Hexane → (S)-3-Butyloxy-4-(1-methyl-2-pyrrolidinylmethoxy)-1,2,5-thiadiazole

HRID 264804

반응식

HRID 264804 반응식
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].C([Li])CCC.CCCCCC.[CH2:20]([O:24][C:25]1[C:29](S(C)(=O)=O)=[N:28][S:27][N:26]=1)[CH2:21][CH2:22][CH3:23]>C1COCC1>[CH2:20]([O:24][C:25]1[C:29]([O:8][CH2:7][C@@H:3]2[CH2:4][CH2:5][CH2:6][N:2]2[CH3:1])=[N:28][S:27][N:26]=1)[CH2:21][CH2:22][CH3:23]

참가 물질

6

반응물 4

HCID 8058HexaneHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanolHCID 196003073-Butyloxy-4-methanesulfonyl-1,2,5-thiadiazoleHCID 178418339Butyllithium

생성물 1

HCID 54562067(S)-3-Butyloxy-4-(1-methyl-2-pyrrolidinylmethoxy)-1,2,5-thiadiazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (S)-1-methyl-2-pyrrolidinemethanol (0.86, 0.0075 mol) in THF (20 mL) was treated with 1.6M n-butyllithium in hexane (4.7 mL, 0.0075 mol). To the solution was added 3-butyloxy-4-methanesulfonyl-1,2,5-thiadiazole (1.2 g, 0.005 mol) and the reaction heated to reflux for 6.5 h. The solvent was evaporated, the residue acidified with cold 1N HCl, and the mixture extracted with ether. The aqueous was made basic and extracted with EtOAc. The extracts were washed with water, dried, and the solvent evaporated to give a liquid. The HCl salt (0.72 g) crystallized from EtOAc, m.p. 115°-116° C. (Compound 31).

후처리

  1. temperaturethe reaction heated
  2. temperatureto reflux for 6.5 h
  3. customThe solvent was evaporated
  4. extractionthe mixture extracted with ether
  5. extractionextracted with EtOAc
  6. washThe extracts were washed with water
  7. customdried
  8. customthe solvent evaporated
  9. customto give a liquid
  10. customThe HCl salt (0.72 g) crystallized from EtOAc, m.p. 115°-116° C. (Compound 31)

출처 및 근거

ORD 기록
ord-710ed8b3c0d6416883409822a55f47ab
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05646289

연결된 노트

불러오는 중…