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

HRID 1856284노트

반응식

HRID 1856284 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 6342Acetonitrile용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-752f413907e34c63b35e5db58f10cc94
출처 데이터셋
uspto-grants-1980_08
특허 번호
US04218472

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