Dichloromethane → HCID 66582488, compound

HRID 1972452Notes

Reaction equation

HRID 1972452 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:15][CH:14]2[N:16](C(OC(C)(C)C)=O)[CH:10]1[CH2:11][O:12][CH2:13]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)Cl.C(O)(C(F)(F)F)=O>C(OCC)C>[CH2:1]([O:8][CH:9]1[CH2:15][CH:14]2[NH:16][CH:10]1[CH2:11][O:12][CH2:13]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 66582731Tert-butyl 6-(benzyloxy)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate

Product 1

HCID 66582488HCID 66582488, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 250-mL round-bottomed flask was charged with tert-butyl 6-(benzyloxy)-3-oxa-8-azabicyclo[3.2.1]octane-8-carboxylate (4.40 g, 13.78 mmol J. Org. Chem. 2010, 75, 1643) and 15 mL of CH2Cl2. To this was added TFA (10.61 mL, 138 mmol). After 2 h at room temperature, the mixture was concentrated and diluted with saturated aqueous NaHCO3 and CH2Cl2. The layers were separated, the organics were dried (MgSO4), filtered, and concentrated to give a white solid. This solid was slurried with 50 mL of diethyl ether. The resulting white solid was collected by filtration to give 6-(benzyloxy)-3-oxa-8-azabicyclo[3.2.1]octane (3.02 g)

Workup

  1. concentrationthe mixture was concentrated
  2. additiondiluted with saturated aqueous NaHCO3 and CH2Cl2
  3. customThe layers were separated
  4. dry with materialthe organics were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a white solid
  8. filtrationThe resulting white solid was collected by filtration

Sources & evidence

ORD record
ord-ef5de350880a44caac9f1d70e5b77457
Source dataset
uspto-grants-2013_04
Patent number
US08431563B2

Reaction notes

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