Diethyl Ether → HCID 54365816, compound

HRID 965207Notes

Reaction equation

HRID 965207 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[NH:7]([C@@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@H:15]1[NH:23][C:24](OCC)=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)C>O1CCCC1>[NH:7]([C@@H:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH2:16][C@H:15]1[NH:23][CH3:24])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 13595717HCID 13595717, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54365816HCID 54365816, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of LiAlH4 (1.35 g, 0.035 mol) in dry tetrahydrofuran (25 ml) under nitrogen was added dropwise a solution of (±) trans-1-anilino-2-ethoxycarbonylaminoindane (3.50 g, 0.012 mol) in dry tetrahydrofuran (25 ml). The mixture was heated under reflux for 3.25 h. After cooling in ice, wet diethyl ether was added to quench excess LiAlH4, followed by a minimum amount of water. The precipitate was removed by filtration, and the filtrate was concentrated in vacuo to give a cream coloured solid (2.64 g) which was purified by recrystallisation to give the title compound as a colourless solid, m.p.121°-122° C. (from diethyl ether).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 3.25 h
  3. temperatureAfter cooling in ice
  4. customto quench excess LiAlH4
  5. customThe precipitate was removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. customto give a cream
  8. customwas purified by recrystallisation

Sources & evidence

ORD record
ord-8aea988319e8484fabdd670559b891b5
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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