Tetrahydrofuran → Tert-butyl 3-cyano-3-hydroxypiperidine-1-carboxylate
Reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C1COCC1.[C-:20]#[N:21].[K+].OS([O-])=O.[Na+]>C(Cl)Cl.O>[C:20]([C:10]1([OH:14])[CH2:11][CH2:12][CH2:13][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:9]1)#[N:21]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of N-Boc-3-piperidone (5.00 g, 25.1 mmol) and THF (15 mL) was added KCN (2.34 g, 37.6 mmol) and H2O (15 mL) and the resulting solution was cooled to 0° C. To the resulting homogeneous orange solution was added a solution of NaHSO3 (1.25 g, 37.6 mmol) and H2O (15 mL). The resulting solution was stirred at 0° C. for 1 hour. The solution was twice extracted DCM and the combined extracts were dried by Na2SO4, filtered and evaporated to afford title compound 5.7 g as white solid. MS (m/z): 127 (M+H-Boc)+
Workup
- dry with materialthe combined extracts were dried by Na2SO4
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-33a2dff70fcf416cba55482a79fa2a08
- Source dataset
- uspto-grants-2016_09
- Patent number
- US09434726B2
Reaction notes
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