Hydrogen oxalate monoanion → 2-Dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol

HRID 1856284Notes

Reaction equation

HRID 1856284 reaction equation
[CH3:1][N:2]([CH3:20])[C:3](=O)[C:4](=[O:18])[C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(O)(=O)C([O-])=O>C(OCC)C.C(#N)C>[CH3:1][N:2]([CH3:20])[CH2:3][CH:4]([C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]2([CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:6]=1)[OH:18]

Participants

6

Reactant 3

HCID 3716971Hydrogen oxalate monoanionHCID 21226445Aluminium lithium hydrideHCID 23346446HCID 23346446, compound

Product 1

HCID 233464542-Dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6342AcetonitrileSolvent

Procedure

The oxoamide from step (a) (2.69) in anhydrous diethyl ether (200 ml) is stirred for 24 hours at about 20° C. with lithium aluminium hydride (2 g) in diethyl ether (100 ml). The excess of hydride is destroyed with saturated aqueous sodium sulphate solution. The ether phase is separated, washed, dried and concentrated to an oil which contains 2-dimethylamino-1-[spiro(cyclopentane-1,1'-indene)-3'-yl]ethanol contaminated by much of the corresponding indanyl analogue. The two compounds are separated by chromatography on aluminium oxide with diethyl ether/methanol as eluent. The product so obtained is converted into the hydrogen oxalate of the title compound in acetonitrile solution. M.p. 133°-134° C.

Workup

  1. customThe excess of hydride is destroyed with saturated aqueous sodium sulphate solution
  2. customThe ether phase is separated
  3. washwashed
  4. customdried
  5. concentrationconcentrated to an oil which
  6. customThe two compounds are separated by chromatography on aluminium oxide with diethyl ether/methanol as eluent
  7. customThe product so obtained

Sources & evidence

ORD record
ord-752f413907e34c63b35e5db58f10cc94
Source dataset
uspto-grants-1980_08
Patent number
US04218472

Reaction notes

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