Water → HCID 25176286, compound

HRID 2366031Notes

Reaction equation

HRID 2366031 reaction equation
C[O:2][C:3]([C:5]1([F:22])[CH2:10][CH2:9][CH2:8][N:7]([CH2:11][CH:12]2[O:17][C:16]3[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=3[O:14][CH2:13]2)[CH2:6]1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[O:17]1[C:16]2[CH:18]=[CH:19][CH:20]=[CH:21][C:15]=2[O:14][CH2:13][CH:12]1[CH2:11][N:7]1[CH2:8][CH2:9][CH2:10][C:5]([CH2:3][OH:2])([F:22])[CH2:6]1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66727150HCID 66727150, compound

Product 1

HCID 25176286HCID 25176286, compoundYield 81.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

1-(2,3-Dihydrobenzo[1,4]dioxin-2-ylmethyl)-3-fluoro-piperidine-3-carboxylic acid methyl ester (145 mg, 0.45 mmol) was dissolved in dry THF (4 ml), cooled to −20° C. and treated with LiAlH4 (34 mg, 0.90 mmol) for 3 h. Water (1 ml), 1 M NaOH (1 ml) and again water (1 ml) was added. The mixture was filtrated, concentrated and extracted with DCM three times. The organic layers were pooled and purified by flash chromatography (gradient of DCM/MeOH) to give 103 mg of the title compound.

Workup

  1. filtrationThe mixture was filtrated
  2. concentrationconcentrated
  3. extractionextracted with DCM three times
  4. custompurified by flash chromatography (gradient of DCM/MeOH)

Sources & evidence

ORD record
ord-e7ee55171a9342b0ab8beae4a3612c1e
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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