Water → HCID 12939919, compound

HRID 443835Notes

Reaction equation

HRID 443835 reaction equation
[C:1]([CH:4]1[NH:9][CH2:8][C:7]2[CH:10]=[CH:11][S:12][C:6]=2[CH2:5]1)(O)=[O:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[OH:2][CH2:1][CH:4]1[NH:9][CH2:8][C:7]2[CH:10]=[CH:11][S:12][C:6]=2[CH2:5]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 12685848(RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridineHCID 21226445Aluminium lithium hydride

Product 1

HCID 12939919HCID 12939919, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(RS)-6-Carboxy-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (3.7 g) is added, under a nitrogen atmosphere and in small portions, to a solution of lithium aluminum hydride (1.1 g) in tetrahydrofuran (45 cc); the resulting suspension is heated under reflux for 4 hours. After cooling, water (1.35 cc), 5N aqueous sodium hydroxide solution (0.95 cc) and water (4.35 cc) are successively added dropwise. The inorganic salts formed are filtered off and washed with methylene chloride (5×20 cc). The filtrates are combined and evaporated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 60° C. The residue is dissolved in boiling acetonitrile (15 cc) and the solution is cooled and then kept at 5° C. for 20 hours. The resulting crystals are filtered off, washed with cyclohexane and dried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa). (RS)-6-Hydroxymethyl-4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1.2 g), melting at 110° C., is thus obtained.

Workup

  1. temperaturethe resulting suspension is heated
  2. temperatureunder reflux for 4 hours
  3. temperatureAfter cooling
  4. customThe inorganic salts formed
  5. filtrationare filtered off
  6. washwashed with methylene chloride (5×20 cc)
  7. customevaporated to dryness under reduced pressure (25 mm Hg; 3.3 kPa) at 60° C
  8. dissolutionThe residue is dissolved
  9. temperaturethe solution is cooled
  10. filtrationThe resulting crystals are filtered off
  11. washwashed with cyclohexane
  12. customdried at 20° C. under reduced pressure (0.1 mm Hg; 0.013 kPa)

Sources & evidence

ORD record
ord-2a38a7c4c78b496f9dbde2517648b599
Source dataset
uspto-grants-1981_04
Patent number
US04261999

Reaction notes

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