1-Aminotetralin, (S)- → (s)-1,2,3,4-Tetrahydronaphthalen-1-aminium (1s,3ar,6as)-2-(t-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

HRID 540974

Reaction equation

HRID 540974 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH:14]2[CH:10]([CH2:11][CH2:12][CH2:13]2)[CH:9]1[C:16]([OH:18])=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C@@H:19]1([NH2:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1>C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@@H:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]2[C@H:9]1[C:16]([O-:18])=[O:17])=[O:7])([CH3:4])([CH3:2])[CH3:3].[C@@H:19]1([NH3+:29])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 70580741-Aminotetralin, (S)-HCID 532496462-(Tert-butoxycarbonyl)octahydrocyclopenta[C]pyrrole-1-carboxylic acid

Product 1

HCID 131731979(s)-1,2,3,4-Tetrahydronaphthalen-1-aminium (1s,3ar,6as)-2-(t-butoxycarbonyl)octahydrocyclopenta[c]pyrrole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
23.5 °C

Procedure

The ethyl acetate solution of racemic N-t-butyloxycarbonyl-3-azabicyclo[3.3.0]octane-2-carboxylic acid from Example 2, Method 2, was added to a solution of (S)-1,2,3,4-tetrahydro-1-naphthylamine (56.7 g, 0.385 mol) in ethyl acetate (300 mL). The mixture was stirred for 3-4 hours at 22-25° C., then filtered, and the solids washed with ethyl acetate (200 mL). The product was dried at 20-30° C. under vacuum for 4 hours to give the title compound.

Workup

  1. filtrationfiltered
  2. washthe solids washed with ethyl acetate (200 mL)
  3. customThe product was dried at 20-30° C. under vacuum for 4 hours

Sources & evidence

ORD record
ord-608fe0dfe61d43f6a5e1ded76efb526c
Source dataset
uspto-grants-2014_10
Patent number
US08871904B2

Linked notes

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