Water → HCID 69000456, compound

HRID 1435140Notes

Reaction equation

HRID 1435140 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]([C@@H:9]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10]2)[CH3:8])[CH2:3][CH2:2]1.[Cl:21][C:22]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=1C=O.[C:31](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[Cl:21][C:22]1[CH:29]=[C:28]([Cl:30])[CH:27]=[CH:26][C:23]=1[CH2:8][N:7]([CH2:9][C@H:13]1[CH2:31][CH2:10][N:11]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:12]1)[CH:4]1[CH2:3][CH2:2][O:1][CH2:6][CH2:5]1

Participants

6

Reactant 4

HCID 962WaterHCID 134042,4-DichlorobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68999643HCID 68999643, compound

Product 1

HCID 69000456HCID 69000456, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of N-(tetrahydro-2H-pyran-4-yl)-1-tert-butyloxycarbonyl-(3R)-pyrrolidine-3-yl-methylamine (0.36 g, 1.26 mmol), 2,4-dichlorobenzaldehyde (0.44 g, 2.52 mmol) and sodium triacetoxyborohydride (0.67 g, 3.15 mmol) in 1,2-dichloroethane (15 ml) is stirred at room temperature for 18 h. Water (2 ml) is added to the reaction mixture and stirring continued for 5 min. The organic phase is separated using a hydrophobic frit and evaporated. The resulting oil is dissolved in methanol and purified using a SCX-2 column (10 g), then washed with methanol. The basic product elutes with methanolic ammonia (2M). Evaporation gives the required compound as a colourless oil.

Workup

  1. stirringstirring
  2. waitcontinued for 5 min
  3. customThe organic phase is separated
  4. customevaporated
  5. dissolutionThe resulting oil is dissolved in methanol
  6. custompurified
  7. washwashed with methanol
  8. customEvaporation

Sources & evidence

ORD record
ord-c94c4d2eef884d43a49e31f1271106e8
Source dataset
uspto-grants-2009_11
Patent number
US07615648B2

Reaction notes

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