Hydrochloric Acid → HCID 18661299, compound

HRID 965246Notes

Reaction equation

HRID 965246 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]([C:11]1[CH:34]=[CH:33][C:14]([O:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C@@H:17]2[NH:25][C:26](OC(C)(C)C)=O)=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].[ClH:35]>O1CCCC1>[ClH:35].[C:7]([C:11]1[CH:34]=[CH:33][C:14]([O:15][C@@H:16]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:18][C@@H:17]2[NH:25][CH3:26])=[CH:13][CH:12]=1)([CH3:10])([CH3:8])[CH3:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 18661300HCID 18661300, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 18661299HCID 18661299, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LiAlH4 (730 mg, 19 mmol) in dry tetrahydrofuran (30 ml) under argon was added dropwise a solution of (±)cis-1-(4-tert-butylphenoxy)-2-tert-butoxycarbonylaminoindane (1.4 g, 3.7 mmol) in dry tetrahydrofuran (60 ml). The reaction was heated at reflux for 3 h then cooled with an ice/water bath and quenched with the minimum of water. The reaction was filtered and dried over MgSO4. Solvents were removed in vacuo and the residue subjected to column chromatography on silica gel eluting with 5% ethanol in chloroform to afford a colourless oil (618 mg,) which was converted to the HCl salt and crystallised to afford the title compound as a white solid. m.p. >218° C. dec. (from methanol-diethyl ether).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 3 h
  3. temperaturethen cooled with an ice/water bath
  4. customquenched with the minimum of water
  5. filtrationThe reaction was filtered
  6. dry with materialdried over MgSO4
  7. customSolvents were removed in vacuo
  8. customto afford a colourless oil (618 mg,) which
  9. customcrystallised

Sources & evidence

ORD record
ord-66ca19619a04431ea2921728303c65f6
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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