tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 58080203, compound

HRID 1527009Notes

Reaction equation

HRID 1527009 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[CH:8]([CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]1)=O>C(Cl)Cl>[C:2]([S@@:5](/[N:7]=[CH:8]/[CH:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:20])([CH3:22])[CH3:21])=[O:17])[CH2:12][CH2:11]1)=[O:6])([CH3:4])([CH3:3])[CH3:1]

Participants

4

Reactant 2

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 58080203HCID 58080203, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a round bottomed flask charged with a magnetic stir bar was added (S)-2-methylpropane-2-sulfinamide (20.46 g, 169 mmol), tert-butyl 4-formylpiperidine-1-carboxylate (30 g, 141 mmol), DCM (300 mL), and Ti(OEt)4 (59.0 ml, 281 mmol). The solution was stirred at room temperature for 3 h before it was quenched with brine (80 mL). The solution was stirred for 30 minutes before filtering. The filter cake was washed with DCM and the filtrate was placed in a separatory funnel and washed with water. The organics layer was dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue solidified to the title compound (29 g, 92 mmol, 65.1% yield) m/z 217.

Workup

  1. additionTo a round bottomed flask charged with a magnetic stir bar
  2. customwas quenched with brine (80 mL)
  3. stirringThe solution was stirred for 30 minutes
  4. filtrationbefore filtering
  5. washThe filter cake was washed with DCM
  6. customthe filtrate was placed in a separatory funnel
  7. washwashed with water
  8. dry with materialThe organics layer was dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1e7a0a21f37d47fb8b304e5368c9f62f
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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