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

HRID 1771227Notes

Reaction equation

HRID 1771227 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>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[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

5

Reactant 2

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

Product 1

HCID 58080203HCID 58080203, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of (S)-2-methylpropane-2-sulfinamide (2.0 g, 16.50 mmol) in THF (8.0 ml) and titanium(IV) ethoxide (17.3 ml, 82.51 mmol) were added sequentially to a solution of tert-butyl 4-formylpiperidine-1-carboxylate (3.70 g, 17.33 mmol) in THF (8.0 ml). The resulting mixture was stirred at r.t for 2 hours. The reaction mixture was poured into ice/water and the suspension filtered. The filtrate was extracted with EtOAc and the organic layer was dried with MgSO4, filtered and the filtrate was concentrated under reduced pressure. The residue was dried under vacuum to provide the title compound (4.45 g, yield: 85%).

Workup

  1. filtrationthe suspension filtered
  2. extractionThe filtrate was extracted with EtOAc
  3. dry with materialthe organic layer was dried with MgSO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was dried under vacuum

Sources & evidence

ORD record
ord-0e07c2e71a8e438c90c357e02a591a65
Source dataset
uspto-grants-2016_02
Patent number
US09248140B2

Reaction notes

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