tert-Butyl methyl ether → HCID 86605036, compound

HRID 2378493Notes

Reaction equation

HRID 2378493 reaction equation
[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][C@H:7](/[C:32](/[CH3:40])=[CH:33]/[C:34]1[N:35]=[C:36]([CH3:39])[S:37][CH:38]=1)[CH2:8][C@@H:9]1[O:11][C@:10]1([CH2:26][O:27][S:28]([CH3:31])(=[O:30])=[O:29])[CH2:12][CH2:13][CH2:14][C@H:15]([CH3:25])[CH2:16][O:17][Si](C(C)(C)C)(C)C)([CH3:4])([CH3:3])[CH3:2].C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C([O-])(O)=O.[Na+].CC(OC)(C)C>C(Cl)Cl.CO>[C:1]([Si:5]([CH3:42])([CH3:41])[O:6][C@H:7](/[C:32](/[CH3:40])=[CH:33]/[C:34]1[N:35]=[C:36]([CH3:39])[S:37][CH:38]=1)[CH2:8][C@@H:9]1[O:11][C@:10]1([CH2:26][O:27][S:28]([CH3:31])(=[O:29])=[O:30])[CH2:12][CH2:13][CH2:14][C@H:15]([CH3:25])[CH2:16][OH:17])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 516892Sodium BicarbonateHCID 86605037HCID 86605037, compound

Product 1

HCID 86605036HCID 86605036, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The crude TBDMS ether XVI (3.79 g, 5.7 mmol) was dissolved in a mixture of CH2Cl2 and CH3OH (1:1 v/v) (140 ml) and treated at 0° C. with 1.33 g (5.73 mmol) of 10-camphorsulfonic acid. The reaction mixture was stirred for 1 h at 0° C. After completion of the deprotection 20 ml of saturated aqueous NaHCO3 were added along with 20 ml of TBME. The layers were separated and the aqueous layer was extracted with TBME (2×20 mL). The combined organic layers were washed with saturated aqueous NaHCO3 (2×20 ml), brine (20 ml), dried over MgSO4 and concentrated under reduced pressure. The crude product XVII (3.11 g) obtained as a yellowish oil was used for the next step without further purification. Rf=0.28 (SiO2, 1:1 heptane-AcOEt).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with TBME (2×20 mL)
  3. washThe combined organic layers were washed with saturated aqueous NaHCO3 (2×20 ml), brine (20 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-43a34fba0cc74bdfac1ab73829b3e03f
Source dataset
uspto-grants-2008_12
Patent number
US07470792B2

Reaction notes

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