Sodium Thiosulfate → HCID 57774373, compound

HRID 1695953Notes

Reaction equation

HRID 1695953 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl.CCOC(C)=O>[CH:2]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]1)=[O:1]

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 57774474Tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate

Product 1

HCID 57774373HCID 57774373, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(2-(hydroxymethyl)phenyl)piperidine-1-carboxylate (216 mg, 0.74 mmol, 1 eq.) and Dess Martin periodinane (377 mg, 1.2 eq., 0.89 mmol) were stirred in DCM (7 mL) for 1 h. HPLC and LCMS showed completion of the reaction. Sodium thiosulfate was then added and the biphasic mixture was stirred for 10 min, then the mixture was diluted with EtOAc (50 mL), the biphasic mixture was separated, the organics were dried (MgSO4), conc in vacuo and purified by ISCO chromatography (8 g SiO2, 0 to 15% EtOAc in Hexanes). Remaining DMP side product was observed so the residue was taken up in DCM, the insolubles filtered off, the filtrate concentrated and purified by ISCO chromatography (12 g SiO2, 0 to 10% EtOAc in Hexanes) to give, after concentration, 229 mg of tert-butyl 4-(2-formylphenyl)piperidine-1-carboxylate as a clear oil (still contains some DMP side product) which was used in the next step without further purification. LC/MS ES+1-Boc: 190.08.

Workup

  1. customcompletion of the reaction
  2. customthe biphasic mixture was separated
  3. dry with materialthe organics were dried (MgSO4)
  4. customconc in vacuo and purified by ISCO chromatography (8 g SiO2, 0 to 15% EtOAc in Hexanes)
  5. filtrationthe insolubles filtered off
  6. concentrationthe filtrate concentrated
  7. custompurified by ISCO chromatography (12 g SiO2, 0 to 10% EtOAc in Hexanes)
  8. customto give
  9. concentrationafter concentration, 229 mg of tert-butyl 4-(2-formylphenyl)piperidine-1-carboxylate as a clear oil (
  10. customwas used in the next step without further purification

Sources & evidence

ORD record
ord-2ecfb821b1774242963170908d1348a3
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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