Sodium Hydroxide → HCID 12621148, compound

HRID 372095Notes

Reaction equation

HRID 372095 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([C:12]([N:14]2[CH2:18][C:17]34[CH2:28][CH:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[C:16]3=[CH:15]2)[C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]4=2)=O)[CH2:11][CH2:10][CH2:9][CH2:8]1.[H-].[OH-].[Na+]>CCOCC.O>[CH:7]1([CH2:12][N:14]2[CH2:18][C:17]34[CH2:28][CH:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=5[C:16]3=[CH:15]2)[C:20]2[CH:29]=[CH:30][CH:31]=[CH:32][C:19]4=2)[CH2:8][CH2:9][CH2:10][CH2:11]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 166653HydrideHCID 12621147HCID 12621147, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12621148HCID 12621148, compoundYield 59.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a cooled slurry of 0.40 g of lithium aluminum hydride in 30 ml of ether is added 1.55 g of 9b and the mixture is stirred at room temperature for 6 hours. The excess hydride is decomposed by the addition of 0.4 ml of water, followed by 0.4 ml of 15% aqueous sodium hydroxide solution and 1.2 ml of water. The mixture is filtered and the filtrate is concentrated. Crystallization of the residue from isopropyl alcohol gives 0.89 g of 2-cyclopentylmethyl-2,3-dihydro-8H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole (8e), identical by infrared and nmr spectroscopy with the product obtained in Example 8. Reduction of 8e as described in Example 8 gives 2-cycopentylmethyl-2,3,8,12b-tetrahydro-1H-3a,8-methanodibenzo[3,4:6,7]cyclohepta[1,2-c]pyrrole.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe filtrate is concentrated
  3. customCrystallization of the residue from isopropyl alcohol

Sources & evidence

ORD record
ord-2780fc6887c841c2862370f566c0de8a
Source dataset
uspto-grants-1978_05
Patent number
US04088772

Reaction notes

Loading…