Trifluoroacetic acid → 1-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidine

HRID 1108028Notes

Reaction equation

HRID 1108028 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][C:14](O)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH2:13][CH:14]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:23][CH3:24])[CH2:15][CH2:16]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 516892Sodium BicarbonateHCID 187863061-Benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine

Product 1

HCID 111106201-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidineYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The product of Step 2 (5.1 g) in CH2Cl2 (50 mL) was treated sequentially with trifluoroacetic acid (8.9 mL) and triethylsilane (34.5 mL). After 18 h, the solution was treated with saturated NaHCO3 (150 mL). After a further 1 h, the organic layer was separated and the aqueous extracted with CH2Cl2 (100 mL). The organic extracts were combined, dried over Na2SO4, filtered and evaporated. The crude product was purified by silica gel chromatography, eluting with EtOAc/hexane mixtures to give 1-benzyloxycarbonyl-4(2-methylthiophenyl)piperidine (3.3 g).

Workup

  1. waitAfter a further 1 h
  2. customthe organic layer was separated
  3. extractionthe aqueous extracted with CH2Cl2 (100 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by silica gel chromatography
  8. washeluting with EtOAc/hexane

Sources & evidence

ORD record
ord-4cb6fe4f100e44b4a103b7312aeb065d
Source dataset
uspto-grants-2000_05
Patent number
US06063926

Reaction notes

Loading…