[3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl]carbamic acid benzyl ester → 3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butylamine

HRID 907617Notes

Reaction equation

HRID 907617 reaction equation
C(OC(=O)[NH:10][C@H:11]([C:17]12[O:24][CH2:23][C:20]([CH3:25])([CH2:21][O:22]1)[CH2:19][O:18]2)[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14])C1C=CC=CC=1>C(OCC)(=O)C>[CH3:14][C:13]([CH3:16])([CH3:15])[CH2:12][C@H:11]([NH2:10])[C:17]12[O:18][CH2:19][C:20]([CH3:25])([CH2:21][O:22]1)[CH2:23][O:24]2

Participants

3

Reactant 1

HCID 67391458[3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl]carbamic acid benzyl ester

Product 1

HCID 673915813,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butylamineYield 84.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

[3,3-Dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butyl]carbamic acid benzyl ester (15 g) was dissolved in ethyl acetate (300 ml) and after degassing with nitrogen, 10% Pd—C (1.5 g) was added under nitrogen atmosphere. The reaction mixture was hydrogenated at 50 psi for 4 h. The solution was filtered through celite and washed with EtOAc. The solvent was removed to give 3,3-dimethyl-1(S)-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)butylamine (8 g) as a white solid.

Workup

  1. customafter degassing with nitrogen, 10% Pd—C (1.5 g)
  2. additionwas added under nitrogen atmosphere
  3. filtrationThe solution was filtered through celite
  4. washwashed with EtOAc
  5. customThe solvent was removed

Sources & evidence

ORD record
ord-fed9549799b0411188cb16c075b66012
Source dataset
uspto-grants-2011_09
Patent number
US08013186B2

Reaction notes

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