Acetic Acid → HCID 67044981, compound
Reaction equation
[CH:1]1([C@@H:4]2[CH2:9][CH2:8][NH:7][CH2:6][C@H:5]2[NH:10][P:11](=[O:18])([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])[CH2:3][CH2:2]1.[CH:19](=O)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O)(=O)C.[BH3-]C#N.[Na+]>CO>[CH2:19]([N:7]1[CH2:8][CH2:9][C@@H:4]([CH:1]2[CH2:2][CH2:3]2)[C@H:5]([NH:10][P:11](=[O:18])([O:12][CH2:13][CH3:14])[O:15][CH2:16][CH3:17])[CH2:6]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A mixture of diethyl trans-4-cyclopropylpiperidin-3-ylphosphoramidate (1.24 g, 4.49 mmol), benzaldehyde (0.68 mL, 6.73 mmol) and acetic acid (0.51 mL, 8.98 mmol) in methanol (20 mL) was stirred at 0° C. for 30 minutes. NaCNBH3 (0.42 g, 6.73 mmol) was added at 0° C. The resulting solution was warmed to room temperature and stirred at room temperature for 1 hour. The solvent was removed in vacuo, and saturated sodium bicarbonate (20 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated in vacuo to give diethyl trans-1-benzyl-4-cyclopropylpiperidin-3-ylphosphoramidate (1.64 g, 100%), which was used directly in the next step without purification.
Workup
- temperatureThe resulting solution was warmed to room temperature
- stirringstirred at room temperature for 1 hour
- customThe solvent was removed in vacuo, and saturated sodium bicarbonate (20 mL) and ethyl acetate (30 mL)
- additionwere added
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried (sodium sulfate)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-09bd04f4f8124154a17f44d3e0f0b275
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08178131B2
Reaction notes
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