Periodate → 1,1-dimethylethyl [[(2S,3S) 3-formyl-1,4-dioxaspiro[4,5]dec-2-yl]methoxy]acetate

HRID 1354496Notes

Reaction equation

HRID 1354496 reaction equation
[OH:1][CH:2]([C@H:6]1[O:10][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:8][C@H:7]1[CH2:16][O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])CCO.I([O-])(=O)(=O)=O>CC(C)=O.O>[CH:2]([C@H:6]1[O:10][C:9]2([CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[O:8][C@H:7]1[CH2:16][O:17][CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[O:1]

Participants

5

Reactant 2

HCID 167232PeriodateHCID 690053221,1-dimethylethyl [[(2S,3R) 3-(1,3-dihydroxypropyl)-1,4-dioxaspiro[4,5]dec-2-yl]methoxy]acetate

Product 1

HCID 865887771,1-dimethylethyl [[(2S,3S) 3-formyl-1,4-dioxaspiro[4,5]dec-2-yl]methoxy]acetateYield 92.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 1,1-dimethylethyl [[(2S,3R) 3-(1,3-dihydroxypropyl)-1,4-dioxaspiro[4,5]dec-2-yl]methoxy]acetate (50 g, 138 mmol) in acetone (350 mL) was treated with a solution of periodate (50 g, 235 mmol, 1.7 eq) in water (1.2 L). The reaction mixture was stirred vigorously under nitrogen and monitored by TLC. After about 4 hours, the reaction was complete by TLC analysis. Acetone was removed under reduced pressure without heating. The reaction mixture was extracted with ethyl acetate (3×500 mL). The combined organic layers were dried and concentrated under reduced pressure without heating to give 40 g of 1,1-dimethylethyl [[(2S,3S) 3-formyl-1,4-dioxaspiro[4,5]dec-2-yl]methoxy]acetate as a clear oil: [α]D=−1.142 (10.147 mg/cc in MeOH); 1H NMR (CDCl3) δ 1.38 (m, 2H), 1.42 (s, 9H), 1.61 (m, 8H), 1.73 (m, 2H), 3.52 (dd, 1 H), 3.72 (dd, 1 H), 3.88 (s, 2H), 4.38 (dd, 1 H), 4.52 (m, 1H), 9.62 (s, 11H) ppm.

Workup

  1. customAcetone was removed under reduced pressure
  2. temperaturewithout heating
  3. extractionThe reaction mixture was extracted with ethyl acetate (3×500 mL)
  4. customThe combined organic layers were dried
  5. concentrationconcentrated under reduced pressure
  6. temperaturewithout heating

Sources & evidence

ORD record
ord-2033f2942444430fa678e9e1b698aa69
Source dataset
uspto-grants-2007_05
Patent number
US07223798B2

Reaction notes

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