HCID 15054017, compound → HCID 19102610, compound

HRID 1198544Notes

Reaction equation

HRID 1198544 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:18](OC)=[O:19])=[C:13]2[C:17]=1[NH:16][CH:15]=[CH:14]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:1]([O:8][C:9]1[C:17]2[NH:16][CH:15]=[CH:14][C:13]=2[C:12]([CH2:18][OH:19])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 15054017HCID 15054017, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19102610HCID 19102610, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 7-benzyloxy-4-(methoxycarbonyl)indole (Example 4a) (2.08 g, 7.4 mmol) was added to a stirred suspension of lithium aluminium hydride (0.38 g, 10 mmol) in tetrahydrofuran (15 ml). The mixture was heated at 50° C. for 1 hour, poured onto ice-hydrochloric acid and extracted with dichloromethane. The extract was dried and evaporated and the residue was chromatographed on silica in ethyl acetate-hexane (1:2 then 1:1) to give a pale oil.

Workup

  1. additionpoured onto ice-hydrochloric acid
  2. extractionextracted with dichloromethane
  3. customThe extract was dried
  4. customevaporated
  5. customthe residue was chromatographed on silica in ethyl acetate-hexane (1:2
  6. custom1:1) to give a pale oil

Sources & evidence

ORD record
ord-b6fc95e9ad394803afa95485f55d86da
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Reaction notes

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