Triacetoxyperiodinane → HCID 86596966, compound

HRID 2225288Notes

Reaction equation

HRID 2225288 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:15][C@H:14]([OH:16])[CH2:13][CH2:12][C@@H:11]1[NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl.CCOCC>[Si:1]([O:8][CH2:9][C@@H:10]1[CH2:15][C:14](=[O:16])[CH2:13][CH2:12][C@@H:11]1[NH:17][C:18](=[O:27])[O:19][CH2:20][C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86596965HCID 86596965, compound

Product 1

HCID 86596966HCID 86596966, compoundYield 98.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

The compound benzyl (1S,2R,4R)-2-((tert-butyldimethylsilyloxy)methyl)-4-hydroxycyclohexylcarbamate (4.15 g) in CH2Cl2 (30 mL) was added to Dess-Martin periodane (13.4 g, 31.6 mmol) in CH2Cl2 (100 mL) at 0° C. After 1 h, the ice bath was removed and the reaction aws stirred overnight. This mixture was diluted with ether (425 mL) and washed with water (2×50 mL), sat'd Na2S2O3 (2×50 mL), 1N sodium hydroxide (2×50 mL), and brine (1×50 mL). The organic layer was dried over MgSO4, filtered, and then evaporated to dryness to give benzyl (1S,2R)-2-((tert-butyldimethylsilyloxy)methyl)-4-oxocyclohexylcarbamate (4.05 g) as a clear viscous oil after drying under vacuum overnight. MS found: (M+H)+=392.

Workup

  1. customthe ice bath was removed
  2. customthe reaction aws
  3. washwashed with water (2×50 mL), sat'd Na2S2O3 (2×50 mL), 1N sodium hydroxide (2×50 mL), and brine (1×50 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-ea1bb997f8f64620a24a32930912f3a6
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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