Methanol → 2-Methyl-2-(pyrrolidin-1-yl)propan-1-ol
Reaction equation
C([O:3][C:4](=O)[C:5]([CH3:12])([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH3:6])C.CO.[BH4-].[Li+]>C1COCC1>[CH3:6][C:5]([N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)([CH3:12])[CH2:4][OH:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 4 °C
Procedure
2-Methyl-2-pyrrolidin-1-yl-propionic acid ethyl ester (2.00 g, 10.8 mmol, 1 eq) was suspended in dry THF (20 mL) under Ar. Methanol (2.0 mL, 50 mmol, 5.0 eq) was added followed by cooling to 4° C. and the addition of lithium borohydride (25 mL of 2M, 50 mmol, 5.0 eq). The reaction mixture was stirred and allowed to warm to room temperature. After 18 hours, the reaction was quenched with methanol, then aqueous NaOH, and extracted with CH2Cl2 (3×). The combined organic extracts were washed with brine and dried over Na2SO4. After removing the solvent, the crude residue was used in the next step.
Workup
- temperatureto warm to room temperature
- customthe reaction was quenched with methanol
- extractionaqueous NaOH, and extracted with CH2Cl2 (3×)
- washThe combined organic extracts were washed with brine
- dry with materialdried over Na2SO4
- customAfter removing the solvent
Sources & evidence
- ORD record
- ord-393e4617e3f74885a4ae9a5f85654363
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06951848B2
Reaction notes
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