Methyl iodide → N-tert-Butyloxycarbonyl-3-thiocarbamoyloxymethyl-1,2,3,4-tetrahydroisoquinoline

HRID 618689Notes

Reaction equation

HRID 618689 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:17]([CH2:18][OH:19])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].CI.[OH-].[NH4+:25].[C:26](=[S:28])=S>O1CCCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[CH:17]([CH2:18][O:19][C:26](=[S:28])[NH2:25])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 14923Ammonium HydroxideHCID 24758Sodium hydrideHCID 12114559N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 9797250N-tert-Butyloxycarbonyl-3-thiocarbamoyloxymethyl-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To N-tert-Butyloxycarbonyl-3-hydroxymethyl-1,2,3,4-tetrahydroisoquinoline (9 g) dissolved in tetrahydrofuran (200 mL) at 0° C. was added sodium hydride (60% in mineral oil 1.64 g). The mixture wa stirred for 50 minutes then, carbon disulfide (2.5 mL) was added and stirred for an additional 1 hour. Then methyl iodide (2.55 mL) was added and after two hours ammonium hydroxide (28% solution, 10.4 mL) was added. After overnight stirring, brine was added, the mixture was extracted with methylene chloride and the extract concentrated to yield the product as a solid (5.6 g).

Workup

  1. stirringstirred for an additional 1 hour
  2. additionwas added
  3. stirringAfter overnight stirring
  4. extractionthe mixture was extracted with methylene chloride
  5. concentrationthe extract concentrated

Sources & evidence

ORD record
ord-52f89d234596461597fdeb2be01875e4
Source dataset
uspto-grants-1999_09
Patent number
US05955471

Reaction notes

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