Diethyl Ether → HCID 22407305, compound

HRID 249251Notes

Reaction equation

HRID 249251 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10](=O)[CH2:11][N:12]([C:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=1[F:28])[N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)C.[Cl-].[NH4+].C(OCC)C>O1CCCC1>[F:28][C:23]1[CH:24]=[N:25][CH:26]=[CH:27][C:22]=1[N:12]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14]1)[CH2:11][CH2:10][OH:9]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 21226445Aluminium lithium hydrideHCID 22407302HCID 22407302, compound

Product 1

HCID 22407305HCID 22407305, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of lithium aluminum hydride (1M solution, 70 ml) cooled to 0° C., was added a solution of N-(3-fluoro-4-pyridinyl)-N-(1H-indol-1-yl)glycine ethyl ester (11.4 g) in 125 ml tetrahydrofuran in thirty minutes. After stirring at 0° C. for one hour, a solution of ammonium chloride was added, followed by 300 ml ethyl ether. The mixture was filtered, and the filtrate evaporated to a solid 10 g; which was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC. The desired fractions were combined, then evaporated to yield 6.1 g of N-(3-fluoropyridin-4-yl)-N-(1H-indol-1-yl)-2-aminoethanol, as a solid, m.p. 133°-5° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated to a solid 10 g
  3. washwhich was eluted on a silica gel column with ethyl acetate/dichloromethane (1:1) via HPLC
  4. customevaporated

Sources & evidence

ORD record
ord-9fa28fdb1e6e4cc79e5a6c7812048ab5
Source dataset
uspto-grants-1993_05
Patent number
US05214038

Reaction notes

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