Water → Fingolimod

HRID 617877Notes

Reaction equation

HRID 617877 reaction equation
[BH4-].[Na+].[Br-].[Li+].[NH2:5][C:6]([C:28](OCC)=[O:29])([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=1)[C:7](OCC)=[O:8].O>C(O)C>[NH2:5][C:6]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[CH:16][CH:15]=1)([CH2:28][OH:29])[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 82050Lithium BromideHCID 4311764Sodium borohydrideHCID 21849165Diethyl 2-Amino-2-(4-Octylphenethyl)malonate

Product 1

HCID 107970FingolimodYield 69.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of sodium borohydride (0.60 g) and lithium bromide (1.66 g) in ethanol (17 ml) was stirred at room temperature for 25 minutes. Ethyl 2-amino-2-ethoxycarbonyl-4-(4-octylphenyl)butyrate (1.24 g) was dropwise added thereto over 3 minutes and the mixture was stirred at room temperature for 5 hours. Water (40 ml) was added to the reaction mixture and the mixture was stirred for 40 minutes. The crystals precipitated was collected by filtration and dried to give 0.68 g of the subject compound, melting point=125-126° C. Treatment of the subject compound with hydrochloric acid-ethanol gives the corresponding hydrochloride.

Workup

  1. waitover 3 minutes
  2. stirringthe mixture was stirred at room temperature for 5 hours
  3. stirringthe mixture was stirred for 40 minutes
  4. customThe crystals precipitated
  5. filtrationwas collected by filtration
  6. customdried

Sources & evidence

ORD record
ord-98356641ac1b41e59520c84aae2d0f4b
Source dataset
uspto-grants-1999_09
Patent number
US05952316

Reaction notes

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