Sodium Hydroxide → HCID 14595968, compound

HRID 1886098Notes

Reaction equation

HRID 1886098 reaction equation
Br.[CH2:2]([N:9]([CH2:11][CH:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:21])[CH3:10])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].[OH-].[Na+]>O1CCCC1>[CH2:2]([N:9]([CH2:11][C@H:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C@H:13]1[OH:21])[CH3:10])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 14595964HCID 14595964, compound

Product 1

HCID 14595968HCID 14595968, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled suspension of 3.46 g (0.01M) of 2,3-dihydro-2-(N-benzyl-N-methyl-aminomethyl)-1H-inden-1-one hydrobromide in 50 ml of dry tetrahydrofuran add 25 ml of a 1M solution of L-Selectride®. Stir the mixture for 1.5 hours and decompose with 5 ml of 10% sodium hydroxide solution. Evaporate the solvent at reduced pressure and distribute the residue between ether and water. Separate the ether layer and extract with dilute hydrochloric acid. Basify the acid extract to yield an oil. Extract the oil into ethyl acetate. Evaporate the solvent and Kugelrohr distill at 90°-100°/0.4 mm to yield 1.78 g (67%) of the title compound [bp=135°-40° C. at 0.3 mmHg].

Workup

  1. customEvaporate the solvent at reduced pressure
  2. customSeparate the ether layer
  3. extractionextract with dilute hydrochloric acid
  4. extractionextract
  5. customto yield an oil
  6. extractionExtract the oil into ethyl acetate
  7. customEvaporate the solvent and Kugelrohr
  8. distillationdistill at 90°-100°/0.4 mm

Sources & evidence

ORD record
ord-d97a1b141f7a41b79f2d33b61e3c838f
Source dataset
uspto-grants-1992_09
Patent number
US05149714

Reaction notes

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