Triacetoxyperiodinane → HCID 58192812, compound

HRID 2092641Notes

Reaction equation

HRID 2092641 reaction equation
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH:12]3[OH:19])[CH2:10]1)[CH2:16]2)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][C:9]12[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([C:12]3=[O:19])[CH2:10]1)[CH2:16]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58192779HCID 58192779, compound

Product 1

HCID 58192812HCID 58192812, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-Hydroxy-adamantan-1-ylmethyl)-carbamic acid tert-butyl ester (1B) (2.81 g, 10 mmol) in 200 mL of DCM was added Dess martin periodinane (5.08 g, 12 mmol) at one portion at rt. The mixture was stirred at rt overnight and was quenched by 20 mL of NH4Cl aq (Sat'd) solution. The mixture was extracted by DCM (5 mL×3) and the combined DCM layers were dried over Na2SO4. Solvent was remove under vacuum and the residue was purified by silica gel chromatography (Hexane:EtOAc 2:1(v/v)) to give the title compounds (3B) (2.52 g, 90%). LC-MS (ESR): m/z=280 (M+H)+.

Workup

  1. customwas quenched by 20 mL of NH4Cl aq (Sat'd) solution
  2. extractionThe mixture was extracted by DCM (5 mL×3)
  3. dry with materialthe combined DCM layers were dried over Na2SO4
  4. customSolvent was remove under vacuum
  5. customthe residue was purified by silica gel chromatography (Hexane:EtOAc 2:1(v/v))

Sources & evidence

ORD record
ord-0f4ac02e65fc462fa078f63f50517d3b
Source dataset
uspto-grants-2013_05
Patent number
US08440720B2

Reaction notes

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