(3S)-2-((tert-butoxy)carbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid → (S)-2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-3-hydroxymethyl-7-hydroxyisoquinoline

HRID 2306892Notes

Reaction equation

HRID 2306892 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@H:17]([C:18](O)=[O:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:21])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[C:1]([O:5][C:6]([N:8]1[C@H:17]([CH2:18][OH:19])[CH2:16][C:15]2[C:10](=[CH:11][C:12]([OH:21])=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 6712312(3S)-2-((tert-butoxy)carbonyl)-7-hydroxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid

Product 1

HCID 69917915(S)-2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-3-hydroxymethyl-7-hydroxyisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-2-t-Butoxycarbonyl-1,2,3,4-tetrahydro-7-hydroxyisoquinoline-3-carboxylic acid (100 mmol) is dissolved in THF (1 L). Borane methyl sulfide complex (200 mmol) is added carefully, and the solution heated at reflux for 1 hour. The solution is cooled, quenched with MeOH, and 1 N HCl to pH 2. The solution is neutralized to pH 7-8 with NaHCO3 and the solvent evaporated. The oily residue is diluted with water, extracted with EtOAC, washed with NaHCO3 and brine, then dried with MgSO4 and evaporated to give the title compound.

Workup

  1. additionBorane methyl sulfide complex (200 mmol) is added carefully
  2. temperaturethe solution heated
  3. temperatureat reflux for 1 hour
  4. temperatureThe solution is cooled
  5. customquenched with MeOH, and 1 N HCl to pH 2
  6. customthe solvent evaporated
  7. additionThe oily residue is diluted with water
  8. extractionextracted with EtOAC
  9. washwashed with NaHCO3 and brine
  10. dry with materialdried with MgSO4
  11. customevaporated

Sources & evidence

ORD record
ord-be23ed0b282342dabf3ca29946671b4b
Source dataset
uspto-grants-2004_12
Patent number
US06828427B1

Reaction notes

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