Potassium;tri(butan-2-yl)boranuide → (3SR,4SR)-1,4-dibenzyl-piperidin-3-ol
Reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:10](=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[K+]>C1COCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:10]([OH:21])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 9.0 g (SR)-1,4-dibenzyl-piperidin-3-one (32 mmol) in 200 ml dry THF were added at −78° C. dropwise 48 ml K-selectride® (1 N in THF, 48 mmol). The reaction mixture was stirred for 1 h at −70° C. and then warmed to r.t. The reaction was quenched by the addition of 100 ml NaHCO3-solution and the aqueous phase was extracted twice with ethyl acetate (200 ml). The combined organic phases were washed with water (100 ml) and brine (100 ml). The organic phase was dried over MgSO4, filtrated and the solvent was removed under reduced pressure to give the crude product. Purification by chromatography (ethyl acetate/hexane 1/2 to 2/1) yielded 6.5 g of the product (23 mmol, 72%) as a yellow oil.
Workup
- temperaturewarmed to r.t
- customThe reaction was quenched by the addition of 100 ml NaHCO3-solution
- extractionthe aqueous phase was extracted twice with ethyl acetate (200 ml)
- washThe combined organic phases were washed with water (100 ml) and brine (100 ml)
- dry with materialThe organic phase was dried over MgSO4
- filtrationfiltrated
- customthe solvent was removed under reduced pressure
- customto give the crude product
- customPurification by chromatography (ethyl acetate/hexane 1/2 to 2/1)
Sources & evidence
- ORD record
- ord-9ad44e8221694e9dad8e8084c18a3b6d
- Source dataset
- uspto-grants-2001_10
- Patent number
- US06310213B1
Reaction notes
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