HCID 13084749, compound → HCID 13084751, compound

HRID 225138Notes

Reaction equation

HRID 225138 reaction equation
[CH2:1]([N:8]1[C:17]2[CH2:16][CH2:15][CH:14]([O:18]C(=O)C3C=CC=CC=3)[CH2:13][C:12]=2[CH2:11][CH2:10][C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28]([N:35]1[C:44]2[CH:39]([CH2:40][CH:41]([O:45]C(=O)C3C=CC=CC=3)[CH2:42][CH:43]=2)[CH2:38][CH2:37][C:36]1=O)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([N:8]1[C:17]2[CH2:16][CH2:15][CH:14]([OH:18])[CH2:13][C:12]=2[CH2:11][CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:28]([N:35]1[C:44]2[CH:39]([CH2:40][CH:41]([OH:45])[CH2:42][CH:43]=2)[CH2:38][CH2:37][CH2:36]1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

5

Reactant 3

HCID 13084749HCID 13084749, compoundHCID 13084750HCID 13084750, compoundHCID 21226445Aluminium lithium hydride

Product 2

HCID 13084751HCID 13084751, compoundHCID 13084752HCID 13084752, compound

Procedure

Following the above sequence of reactions, a mixture of 1-n-propyl-6-benzoyloxy-3,4,5,6,7,8-hexahydro-2(1H)-quinolinone and the corresponding 3,4,4a,5,6,7-hexahydro isomer were first reduced with lithium aluminum hydride to yield a mixture of Δ4a and Δ8 1-n-propyl-6-hydroxyoctahydroquinolines which was converted by treatment with ethereal hydrogen chloride to the enamine hydrochloride. Reduction of this intermediate enamine hydrochloride with sodium cyanoborohydride yielded trans-dl-1-n-propyl-6-hydroxydecahydroquinoline (56 g. of starting material yielded 30 g. of product). Also following the above procedure, 1-benzyl-6-benzoyloxy-3,4,5,6,7,8-hexahydro-2-(1H)-quinolinone in admixture with 1-benzyl-6-benzoyloxy-3,4,4a,5,6,7-hexahydro-2(1H)-quinolinone was reduced with lithium aluminum hydride to yield the corresponding 1-benzyl-6-hydroxy-1,2,3,4,5,6,7,8-octahydroquinoline and 1-benzyl-6-hydroxy-1,2,3,4,4a,5,6,7-octahydroquinoline as a mixture, treatment of which with ethereal hydrogen hydrochloride yielded the enamine salt. Reduction of the enamine salt with sodium cyanoborohydride gave 1-benzyl-6-hydroxydecahydroquinoline (65 g. of starting mixture yielded 49.6 g. of final product).

Sources & evidence

ORD record
ord-1a2d92d3a2c546f4b187f255779d0588
Source dataset
uspto-grants-1980_11
Patent number
US04235909

Reaction notes

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