Water → HCID 58046547, compound

HRID 706366Notes

Reaction equation

HRID 706366 reaction equation
[N:1]([N:3]1[C:26]2[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=2)[C:5]2([CH2:10][CH2:9][N:8]([CH2:11]/[CH:12]=[CH:13]/[C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:7][CH2:6]2)[CH2:4]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[NH2:1][N:3]1[C:26]2[C:21](=[CH:22][C:23]([F:27])=[CH:24][CH:25]=2)[C:5]2([CH2:10][CH2:9][N:8]([CH2:11]/[CH:12]=[CH:13]/[C:14]3[CH:15]=[CH:16][C:17]([Cl:20])=[CH:18][CH:19]=3)[CH2:7][CH2:6]2)[CH2:4]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 58046575HCID 58046575, compound

Product 1

HCID 58046547HCID 58046547, compoundYield 105.8%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-nitroso-5-fluoro-1′-[trans-3-(4-chlorophenyl)allyl]spiro[indoline-3,4′-piperidine] (5 g) in tetrahydrofuran (60 ml) was added dropwise to a suspension of lithium aluminium hydride (1.47 g) in tetrahydrofuran (60 ml) at 0° C. and the resulting mixture was stirred at room temperature for 2.5 hours. Water (4.8 ml) was carefully added, followed by 15% aqueous sodium hydroxide (4.8 ml), and finally water (14.4 ml). The mixture was stirred for 0.5 hours, diluted with ethyl acetate, dried over sodium sulfate, and filtered. The solvents were evaporated in vacuo to afford 5.1 g (100%) of the desired amino-indoline as a solid. MS (ES+) 372.

Workup

  1. stirringThe mixture was stirred for 0.5 hours
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-d086ea3f751c4b6f9dbc56e3293976f4
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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