Hydrochloric Acid → HCID 21847890, compound

HRID 618688Notes

Reaction equation

HRID 618688 reaction equation
C(O[C:6]([N:8]1[C:17]([C:19](OCC)=[O:20])([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl.O=[Si]=O>O1CCCC1>[OH:20][CH2:19][C:17]1([CH3:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][N:8]1[CH3:6]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24261SilicaHCID 12088877HCID 12088877, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 21847890HCID 21847890, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-tert-Butyloxycarbonyl-3-ethoxycarbonyl-3-methyl-1,2,3,4-tetrahydroisoquinoline (10 g) was dissolved in 100 mL of tetrahydrofuran and lithium aluminum hydride (3.42g) was added carefully at 0° C. and the mixture was stirred for 30 min. Then, it was refluxed for 3 h and the reaction mixture was poured onto ice portion wise. The mixture was acidified to pH 1 by 2N HCl (2000 mL) and fltered over Celite 545. Volatile components in the resulting clear solution was evaporated in vacuo and after addition of 100 mL brine, it was extracted with dichloromethane (100 mL×3). Combined organic layer was dried over MgSO4, filtered and concentrated to afford the product as yellow solid (5.98 g)

Workup

  1. temperatureThen, it was refluxed for 3 h
  2. additionthe reaction mixture was poured onto ice portion wise
  3. customVolatile components in the resulting clear solution was evaporated in vacuo
  4. additionafter addition of 100 mL brine, it
  5. extractionwas extracted with dichloromethane (100 mL×3)
  6. dry with materialCombined organic layer was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-f3f1fb85f9f44bb0bfca1d5ac24aeb6c
Source dataset
uspto-grants-1999_09
Patent number
US05955471

Reaction notes

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