Water → HCID 21833753, compound

HRID 1741084Notes

Reaction equation

HRID 1741084 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:27][CH2:26][CH2:25][C:14]3([CH2:19][CH2:18][N:17]([C:20](OCC)=O)[CH2:16][CH2:15]3)[C:12]=2[CH:13]=1.O.[OH-].[Na+]>C1COCC1>[NH2:7][C:8]1[CH:9]=[CH:10][C:11]2[O:27][CH2:26][CH2:25][C:14]3([CH2:19][CH2:18][N:17]([CH3:20])[CH2:16][CH2:15]3)[C:12]=2[CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydride2×HCID 21833717HCID 21833717, compound

Product 1

HCID 21833753HCID 21833753, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A stirred suspension of lithium aluminium hydride (76 mg, 0.0020 mole) in THF (15 ml) at 0° C. under argon was treated with a solution of 6-amino-2,3-dihydro-1'-ethoxycarbonylspiro[4H-benzopyran-4,4'-piperidine] (D104, 300 mg, 0.0010 mole) in THF (5 ml). The reaction mixture was allowed to warm to room temp. and stir for 1.5 h, then treated with more lithium aluminium hydride (38 mg, 0.0010 mole) suspended in THF (5 ml). The mixture was heated under reflux for 0.75 h, then cooled in an ice bath and treated with water (0.10 ml), 10% NaOH solution (0.10 ml) and water (0.30 ml). The resulting mixture was filtered through kieselguhr and the filtrate concentrated in vacuo to afford the title compound as a yellow oil (200 mg, 84%).

Workup

  1. temperatureto warm to room temp.
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 0.75 h
  4. temperaturecooled in an ice bath
  5. filtrationThe resulting mixture was filtered through kieselguhr
  6. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-507546fd787f4bf0bc20330d3ecb2948
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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