Hydrochloric Acid → methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

HRID 708563

반응식

HRID 708563 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[CH2:8][NH:7][C@H:6]([C:13]([OH:15])=[O:14])[CH2:5]2.Cl.[CH3:17]O>>[CH3:17][O:14][C:13]([C@@H:6]1[CH2:5][C:4]2[C:9](=[CH:10][C:11]([OH:12])=[C:2]([OH:1])[CH:3]=2)[CH2:8][NH:7]1)=[O:15]

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 12926159(3S)-6,7-Dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

생성물 1

HCID 6352721methyl (3S)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate

실험 절차

(S)-6,7-Dihydroxy-1,2,3,4-tetrahydro-isoquinoline-3-carboxylic acid (62 g), 200 mL anhydrous MeOH, and 26 mL concentrated hydrochloric acid were stirred together overnight at 70° C. The mixture was then evaporated and the residue resuspended in 500 mL acetonitrile with vigorous stirring to wash all the solid material. Stirring continued for 18 h at r.t., after which the solid product was collected by filtration, washed with 100 mL acetonitrile, and dried under vacuum overnight. Yield 77 g (quantitative). 1H NMR (400 MHz, MeOH-d4): 6.64 (s, 1H), 6.61 (s, 1H), 4.42-4.36 (m, 1H), 4.29-4.24 (m, 2H), 3.89 (s, 3H), 3.29-3.22 (m, 1H), 3.11-3.02 (m, 1H).

후처리

  1. customThe mixture was then evaporated
  2. washto wash all the solid material
  3. stirringStirring
  4. filtrationafter which the solid product was collected by filtration
  5. washwashed with 100 mL acetonitrile
  6. customdried under vacuum overnight

출처 및 근거

ORD 기록
ord-aaffa9a8d51849c59b9321d3b50dafda
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09175003B2

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