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

HRID 2256047Notes

Reaction equation

HRID 2256047 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>ClCCl>[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

5

Reactant 3

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

Product 1

HCID 111106201-Benzyloxycarbonyl-4(2-methylthiophenyl)piperidineYield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-benzyloxycarbonyl-4-hydroxy-4-(2-methylthiophenyl)piperidine (2.89 g) in dichloromethane (80 mL) was treated with 6.2 mL of trifluoroacetic acid followed by 25.7 mL of triethylsilane and stirred for 16 hours. At the end of this period, the volatile material was distilled under reduced pressure and the resulting residue was chromatographed. Elution with 3:1 hexane:ethyl acetate afforded the named material (2.02 g); MS: 342(M+1); NMR: 1.5-1.6 (br, 2), 1.8-1.9 (m, 2), 2.45 (s, 3), 2.8-2.9 (m, 2), 3.1-3.2 (m, 1), 4.3 (br, 2), 5.1 (s, 2), 7.1-7.2 (m, 2), 7.2-7.3 (m, 2), 7.3-7.4 (m, 5).

Workup

  1. distillationAt the end of this period, the volatile material was distilled under reduced pressure
  2. customthe resulting residue was chromatographed
  3. washElution with 3:1 hexane

Sources & evidence

ORD record
ord-8f134aca121a406092782b85fc84cc34
Source dataset
uspto-grants-1997_08
Patent number
US05654299

Reaction notes

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