Sodium triacetoxyborohydride → 1-(Methoxymethyl)-1,2,3,4-tetrahydroisoquinoline

HRID 482459Notes

Reaction equation

HRID 482459 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:15][O:16][CH2:17][C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][N:19]=1>CO>[CH3:15][O:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH2:21][CH2:20][NH:19]1

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 12415172HCID 12415172, compound

Product 1

HCID 183157521-(Methoxymethyl)-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium triacetoxyborohydride (8.11 g, 38.3 mmol) was added to a stirred, ice-cooled solution of the product from (b) above (6.1 g, 34.8 mmol) in methanol (80 ml), then the resulting mixture stirred for 18 hours at room temperature before being quenched with water. The bulk of the solvent was removed under reduced pressure, then the residue basified with 1M aqueous sodium hydroxide solution and extracted with dichloromethane. The extract was washed with saturated brine, dried (MgSO4) and evaporated under reduced pressure to furnish the required product (6.19 g) as an orange oil, Rf 0.25 (SS 3), m/e 178 (M+H)+, which was used without further purification in the next step.

Workup

  1. custombefore being quenched with water
  2. customThe bulk of the solvent was removed under reduced pressure
  3. extractionextracted with dichloromethane
  4. washThe extract was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-913368ece77a44b68aecc89401737933
Source dataset
uspto-grants-1998_08
Patent number
US05798352

Reaction notes

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