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

HRID 1856284ノート

反応式

HRID 1856284 の反応式
[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]

参加物

6

反応物 3

HCID 3716971Hydrogen oxalate monoanionHCID 21226445Aluminium lithium hydrideHCID 23346446HCID 23346446、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-752f413907e34c63b35e5db58f10cc94
出典データセット
uspto-grants-1980_08
特許番号
US04218472

反応ノート

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