Ethanol → HCID 13653084, compound

HRID 1732133Notes

Reaction equation

HRID 1732133 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]1[CH2:10][NH:9][C@H:8]([C:16](OC)=[O:17])[CH2:7][C:6]2=1.[BH4-].[Na+].C(O)C>O>[OH:17][CH2:16][C@@H:8]1[CH2:7][C:6]2[C:5]3[C:13](=[CH:14][CH:15]=[C:3]([F:2])[CH:4]=3)[NH:12][C:11]=2[CH2:10][NH:9]1

Participants

5

Reactant 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 13653070HCID 13653070, compound

Product 1

HCID 13653084HCID 13653084, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.577 g of methyl (3S)-6-fluoro-1,2,3,4-tetrahydro-β-carboline-3-carboxylate hydrochloride, 0.32 g of sodium borohydride, 20 ml of ethanol and 10 ml of water is stirred at room temperature for 21 hours, and then further refluxed for 3 hours. After the reaction, insoluble materials are removed by filtration and washed with hot ethanol. The filtrate and washings are combined and concentrated. Water is added to the residue, and crystalline precipitates are collected by filtration and dried, whereby 286 mg of (3S)-3-hydroxymethyl-6-fluoro-1,2,3,4-tetrahydro-β-carboline are obtained as colorless needles. Yield: 65%

Workup

  1. temperaturefurther refluxed for 3 hours
  2. customAfter the reaction, insoluble materials
  3. customare removed by filtration
  4. washwashed with hot ethanol
  5. concentrationconcentrated
  6. additionWater is added to the residue
  7. customcrystalline precipitates
  8. filtrationare collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-7b3db535d3554275906d83bb3facd803
Source dataset
uspto-grants-1986_11
Patent number
US04625032

Reaction notes

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