Water → HCID 70654078, compound

HRID 1183016Notes

Reaction equation

HRID 1183016 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][CH:7]([CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:20][C@@H:21]2[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]2)=[CH:15][CH:14]=1)[C:8]#[N:9].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C(OCC)C>[CH3:1][O:2][C:3]1[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[CH:28][C:4]=1[CH2:5][NH:6][CH:7]([CH2:10][CH2:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH2:20][C@@H:21]2[CH2:25][O:24][C:23]([CH3:27])([CH3:26])[O:22]2)=[CH:17][CH:18]=1)[CH2:8][NH2:9]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 669170122-(2,4-Dimethoxy-benzylamino)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile

Product 1

HCID 70654078HCID 70654078, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

To a solution of 2-(2,4-dimethoxy-benzylamino)-5-[4-((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-phenyl]-pentanenitrile (513 mg, 1.12 mmol) in diethyl ether (15 mL) under argon is slowly added lithium aluminium hydride (2.25 mL of a 1.0 M solution in diethyl ether, 2.25 mmol). The resulting reaction mixture is stirred at RT for 3 h, then is left standing at RT overnight. Water (0.1 mL) is added cautiously, followed by sodium hydroxide (0.2 mL of a 15% aqueous solution) and a further portion of water (0.1 mL). The reaction mixture is diluted with diethyl ether (5 mL) and then dried over MgSO4 and the solvent is concentrated in vacuo to afford the title compound as a pale yellow oil that is used without further purification. [M+H]+ 459.

Workup

  1. customThe resulting reaction mixture
  2. waitis left
  3. waitstanding at RT overnight
  4. dry with materialdried over MgSO4
  5. concentrationthe solvent is concentrated in vacuo

Sources & evidence

ORD record
ord-0d3c3f2b433d4c6588e860ea262e3b31
Source dataset
uspto-grants-2014_03
Patent number
US08664228B2

Reaction notes

Loading…