Potassium Carbonate → 6-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline

HRID 397034

反応式

HRID 397034 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[N:14](C(=O)C(F)(F)F)[CH2:13][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O.CO>CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]([C:19]1[CH:24]=[CH:23][C:22]([O:25][CH2:26][CH2:27][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)=[CH:21][CH:20]=1)[NH:14][CH2:13][CH2:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 181723851-{6-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2-yl}-2,2,2-trifluoroethanoneHCID 21584119Ethylacetate methanol

生成物 1

HCID 181724176-Benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-1,2,3,4-tetrahydroisoquinoline収率 95%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 1-{6-benzyloxy-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]-3,4-dihydro-1H-isoquinolin-2yl}-2,2,2-trifluoroethanone (1.088 g, 2.1 mmol) and anhydrous K2CO3 (2.861 g, 20.7 mmol) in MeOH (150 ml) was refluxed under N2 for 18 hr, then evaporated in vacuo to a yellow residue. This was dissolved in H2O (25 ml) and extracted with EtOAc (3×50 ml). The combined extracts were dried over MgSO4, and concentrated in vacuo to give 0.881 g of crude yellow product. Purification by flash chromatography, eluting first with EtOAc:MeOH (8:2), then with EtOAc:MeOH (1:1) gave 0.842 g (95% yield) of yellow oil.

後処理

  1. temperaturewas refluxed under N2 for 18 hr
  2. customevaporated in vacuo to a yellow residue
  3. dissolutionThis was dissolved in H2O (25 ml)
  4. extractionextracted with EtOAc (3×50 ml)
  5. dry with materialThe combined extracts were dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customto give 0.881 g of crude yellow product
  8. customPurification by flash chromatography
  9. washeluting first with EtOAc:MeOH (8:2)

出典と根拠

ORDレコード
ord-05b5e2b5b13f42ebb02536dc697125e9
出典データセット
uspto-grants-2003_08
特許番号
US06608203B2

関連ノート

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