Cyclopentanecarbonyl chloride → HCID 86733868, compound

HRID 1283991Notes

Reaction equation

HRID 1283991 reaction equation
CC1(C)C2C=C(O)C=CC=2C[C@H]2[C@@H]1CCCN2.C1(C(Cl)=O)CCCC1.[CH:26]1([C:31]([N:33]2[C@@H:42]3[C@@H:37]([C:38]([CH3:56])([CH3:55])[C:39]4[CH:46]=[C:45]([O:47]C(C5CCCC5)=O)[CH:44]=[CH:43][C:40]=4[CH2:41]3)[CH2:36][CH2:35][CH2:34]2)=O)[CH2:30][CH2:29][CH2:28][CH2:27]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.N1C=CC=CC=1>[CH:26]1([CH2:31][N:33]2[C@@H:42]3[C@@H:37]([C:38]([CH3:56])([CH3:55])[C:39]4[CH:46]=[C:45]([OH:47])[CH:44]=[CH:43][C:40]=4[CH2:41]3)[CH2:36][CH2:35][CH2:34]2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

7

Reactant 4

HCID 78284Cyclopentanecarbonyl chlorideHCID 21226445Aluminium lithium hydrideHCID 86733867HCID 86733867, compoundHCID 86733869HCID 86733869, compound

Product 1

HCID 86733868HCID 86733868, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 6.92 g. of cis-1,2,3,4,4a,5,10,10a-octahydro-5,5-dimethylbenzo[g]quinolin-7-ol in 120 ml. of warm pyridine there was added dropwise 8.78 g. of cyclopentanecarbonyl chloride and the resulting reaction mixture was stirred for five and one-half hours. The reaction mixture was worked up, using partitioning between water and diethyl ether, in a manner similar to that described in Example 13 to yield approximately 12 g. of crude cis-1,2,3,4,4a,5,10,10a-octahydro-1-cyclopentanecarbonyl-5,5-dimethyl-7-cyclopentanecarbonyloxybenzo[g]quinoline in which some solvent remained. This product in 75 ml. of tetrahydrofuran was added dropwise to 1.25 g. of lithium aluminum hydride in 25 ml. of tetrahydrofuran. After this addition was completed, the reaction mixture was stirred and refluxed for 3 hours. The reaction mixture was then worked up to yield crude cis-1,2,3,4,4a,5,10,10a-octahydro-1-(cyclopentylmethyl)-5,5-dimethylbenzo[g]quinolin-7-ol which was converted to the p-toluenesulfonate salt, and off-white solid melting at 220°-222°C.

Workup

  1. customusing partitioning between water and diethyl ether, in a manner similar to
  2. customto yield approximately 12 g
  3. additionAfter this addition
  4. stirringthe reaction mixture was stirred
  5. temperaturerefluxed for 3 hours

Sources & evidence

ORD record
ord-b6834223fef34f03a3befb0fe3c49c9b
Source dataset
uspto-grants-1976_08
Patent number
US03976653

Reaction notes

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