HCID 19359917, compound → Tricyclohexyl [o-(1-aminoethyl)phenyl]tin

HRID 376827Notes

Reaction equation

HRID 376827 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]1([Sn:13]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)([CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:20]([N:22]=[N+]=[N-])[CH3:21])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1>C(OCC)C>[CH:25]1([Sn:13]([CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]2)([CH:7]2[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH:20]([NH2:22])[CH3:21])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1

Participants

4

Reactant 2

HCID 19359917HCID 19359917, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 86755109Tricyclohexyl [o-(1-aminoethyl)phenyl]tinYield 76.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To the mixture of 486 mg of lithium aluminum hydride (12.3 mmol) and 20 ml of diethylether in a 100 ml two-neck flask, 20 ml of a diethylether solution containing 643 mg of tricyclohexyl[o-(1-azidoethyl)phenyl]tin (1.25 mmol) was added dropwise, followed by a heat-refluxing for 11.5 hours. Upon completion of the reaction, the organic layer was separated using 10 ml of water. After the ether layer was washed with 30 ml of a saturated brine and dried over sodium sulfate, the solvent was removed under reduced pressure to yield a crude product. The resultant crude product was purified by column chromatography on silica gel (for which, 25 g of silica gel, and hexane as a development solvent were employed) to yield 467 mg of the final product (yield=76.5%).

Workup

  1. additionwas added dropwise
  2. customheat-refluxing for 11.5 hours
  3. customUpon completion of the reaction
  4. customthe organic layer was separated
  5. washAfter the ether layer was washed with 30 ml of a saturated brine
  6. dry with materialdried over sodium sulfate
  7. customthe solvent was removed under reduced pressure
  8. customto yield a crude product
  9. customThe resultant crude product was purified by column chromatography on silica gel (for which, 25 g of silica gel, and hexane as a development solvent

Sources & evidence

ORD record
ord-d296a101d60844b6911c2d9f4b075f93
Source dataset
uspto-grants-2000_02
Patent number
US06022822

Reaction notes

Loading…