2-(4-(tert-Butoxycarbonyl)piperazin-1-yl)propanoic acid → Tert-butyl 4-(1-hydroxypropan-2-yl)piperazine-1-carboxylate
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH:14]([CH3:18])[C:15](O)=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1>[OH:16][CH2:15][CH:14]([N:11]1[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:9][CH2:10]1)[CH3:18]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
A 1M solution of borane tetrahydrofuran complex (12.00 mL, 12.00 mmol) in THF, was added dropwise to a stirred suspension of 2-(1-tert-butoxycarbonylpiperazin-4-yl)propionic acid (2.58 g, 10 mmol) in tetrahydrofuran (50 mL) at 0° C., over a period of 10 mins under nitrogen. The resulting solution was stirred at 60° C. for 8 h. This was quenched with acetic acid/water (10 ml, 1:2 mixture) and evaporated to dryness. The residue was dissolved in ethyl acetate (50 ml), washed with saturated sodium bicarbonate (25 ml) and water, dried over MgSO4, filtered and evaporated to dryness to give tert-butyl 4-(1-hydroxypropan-2-yl)piperazine-1-carboxylate (0.810 g, 33.2%)
Workup
- customThis was quenched with acetic acid/water (10 ml, 1:2 mixture)
- customevaporated to dryness
- dissolutionThe residue was dissolved in ethyl acetate (50 ml)
- washwashed with saturated sodium bicarbonate (25 ml) and water
- dry with materialdried over MgSO4
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-685cd1e0359a40c1a4d29e642a6d5327
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07737149B2
Reaction notes
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