Hydrochloric Acid → cis 5,6-dihydro-6-(2-ethoxycarbonylethyl)-4-(4-methoxybenzylamino)-4H-thieno[2,3-b]thiopyran

HRID 2254311노트

반응식

HRID 2254311 반응식
O=[C:2]1[CH:7](CCC(OCC)=O)[CH2:6][S:5][C:4]2[S:15][CH:16]=[CH:17][C:3]1=2.[CH3:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24][NH2:25])=[CH:22][CH:21]=1.[BH4-].[Na+].Cl.[CH3:31][CH2:32][OH:33]>C1COCC1.C1(C)C=CC=CC=1.[Ti](Cl)(Cl)(Cl)Cl>[CH2:32]([O:33][C:20]([CH2:21][CH2:22][C@H:6]1[S:5][C:4]2[S:15][CH:16]=[CH:17][C:3]=2[C@@H:2]([NH:25][CH2:24][C:23]2[CH:26]=[CH:27][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[CH2:7]1)=[O:19])[CH3:31]

참가 물질

9

반응물 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 754524-MethoxybenzylamineHCID 4311764Sodium borohydrideHCID 678831665,6-Dihydro-4-oxo-5-(2-ethoxycarbonylethyl)thieno[2,3-b]thiopyran

생성물 1

HCID 86747095cis 5,6-dihydro-6-(2-ethoxycarbonylethyl)-4-(4-methoxybenzylamino)-4H-thieno[2,3-b]thiopyran

시약·촉매·용매 3

HCID 24193Titanium Tetrachloride촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2 (10.4 g, 0.039 mol) in THF (110 ml) and toluene (110 ml) at 0° is added 4-methoxybenzylamine (25.5 ml, 26.8 g, 0.195 mol). Titanium tetrachloride (2.2 ml, 3.8 g, 0.02 mol) is added to the cold solution and the resulting mixture is stirred for 0.75-1 hour. The mixture is added to a cold (0°) stirred suspension of NaBH4 (4.5 g, 0.12 mol) in EtOH (900 ml). The resulting mixture is stirred for about 1 hour and acidified to pH 1 with 3N HCl. The solvent is removed in vacuo and the residue partitioned between EtOAc and saturated NaHCO3 solution. The EtOAc layer is separated, dried and concentrated to dryness to yield 3 wherein R1, R2, R3 and R4 are each H.

후처리

  1. additionThe mixture is added to a cold (0°)
  2. stirringstirred
  3. stirringThe resulting mixture is stirred for about 1 hour
  4. customThe solvent is removed in vacuo
  5. customthe residue partitioned between EtOAc and saturated NaHCO3 solution
  6. customThe EtOAc layer is separated
  7. customdried
  8. concentrationconcentrated to dryness
  9. customto yield 3 wherein R1, R2, R3 and R4

출처 및 근거

ORD 기록
ord-68e0aeaf7c0440b7bf7780fc3524c4be
출처 데이터셋
uspto-grants-1993_08
특허 번호
US05235059

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