tert-Butanol → HCID 21487034, compound

HRID 1414347Notes

Reaction equation

HRID 1414347 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)(C)(C)C.[C:12]([N:16]1[CH:21]2[CH2:22][CH2:23][CH:17]1[CH2:18][C:19](=[O:24])[CH2:20]2)([O:14][CH3:15])=[O:13]>C(OCC)C>[C:12]([N:16]1[CH:17]2[CH2:23][CH2:22][CH:21]1[CH2:20][CH:19]([OH:24])[CH2:18]2)([O:14][CH3:15])=[O:13]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 21226445Aluminium lithium hydrideHCID 21487037HCID 21487037, compound

Product 1

HCID 21487034HCID 21487034, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under nitrogen atmosphere, 11.4 mg of LiAlH4, 0.15 ml of tetrahydrofran and then 85 μl of t-butylalcohol were placed in a reaction vessel. After standing the resulting mixture for 15 min. at room temperature, a tetrahydrofran solution of N-carbomethoxy-8-azabicyclo(3,2,1)octan-3-one prepared by the method as described in Referencial Example 3 (0.1 ml/2 mg) was added to the mixture and then continued stirring for 17.5 hrs.. To the reaction mixture, a moisture contained ethyl ether was added to stop the reaction and then the reaction mixture was subjected to extraction in several times with use of ethyl acetate. The combined extract was dried with use of Na2SO4 and concentrated to obtain N-carbomethoxy-8-azabicyclo(3,2,1)octan-3-ol, in crystal form.

Workup

  1. customfor 15 min.
  2. customat room temperature
  3. additionwas added to the mixture
  4. additionwas added
  5. customthe reaction
  6. extractionthe reaction mixture was subjected to extraction in several times with use of ethyl acetate
  7. extractionThe combined extract
  8. dry with materialwas dried with use of Na2SO4
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-807a93d1b86d41358715ae0554268b46
Source dataset
uspto-grants-1977_01
Patent number
US04001249

Reaction notes

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