Sodium → HCID 13361844, compound

HRID 2413485Notes

Reaction equation

HRID 2413485 reaction equation
[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:14])[CH:10]=2)[CH2:5]1)[CH:2]=[CH2:3].[Na].CS(O[CH2:21][CH:22]1[CH2:26][O:25][C:24]([C:33]2[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=2[Cl:40])([CH2:27][N:28]2[CH:32]=[CH:31][N:30]=[CH:29]2)[O:23]1)(=O)=O>C(O)C>[CH2:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:14][CH2:21][CH:22]3[CH2:26][O:25][C:24]([C:33]4[CH:38]=[CH:37][C:36]([Cl:39])=[CH:35][C:34]=4[Cl:40])([CH2:27][N:28]4[CH:32]=[CH:31][N:30]=[CH:29]4)[O:23]3)[CH:10]=2)[CH2:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 11177254HCID 11177254, compoundHCID 13361817HCID 13361817, compound

Product 1

HCID 13361844HCID 13361844, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.89 g of 2-allyl-6-hydroxy-1,2,3,4-tetrahydroisoquinoline are added to a freshly prepared solution of alcoholate from 0.23 g of sodium in 30 ml of dry ethanol, the mixture is stirred for 15 minutes, 4.07 g of (2RS,4SR)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethyl methanesulfonate are added, and the mixture is then heated under reflux for 8 hours. After cooling, the ethanol is removed in a rotary evaporator, and the residue is taken up with a mixture of 50 ml of water and 50 ml of methylene chloride. The organic phase is shaken twice more with water, dried over magnesium sulfate and evaporated in a rotary evaporator. The residue is purified by column chromatography on silica gel using a mixture of ethyl acetate/methanol 4:1. 1.3 g of a colorless resin (26% of theory) which gradually crystallizes is obtained. Melting point 94°-95° C.

Workup

  1. temperaturethe mixture is then heated
  2. temperatureunder reflux for 8 hours
  3. temperatureAfter cooling
  4. customthe ethanol is removed in a rotary evaporator
  5. additionthe residue is taken up with a mixture of 50 ml of water and 50 ml of methylene chloride
  6. stirringThe organic phase is shaken twice more with water
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in a rotary evaporator
  9. customThe residue is purified by column chromatography on silica gel using
  10. additiona mixture of ethyl acetate/methanol 4:1
  11. custom1.3 g of a colorless resin (26% of theory) which gradually crystallizes
  12. customis obtained

Sources & evidence

ORD record
ord-d4a15cb0ac8c408b82fc3974ce342c1c
Source dataset
uspto-grants-1988_01
Patent number
US04717724

Reaction notes

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