Ammonia → HCID 57588245, compound

HRID 1782057Notes

Reaction equation

HRID 1782057 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]2[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]2[O:26][CH3:27])(=O)=O)=CC=1.[NH3:28]>C1COCC1>[NH2:28][CH2:12][C@@H:13]1[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][C@H:14]1[O:26][CH3:27]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57588246HCID 57588246, compound

Product 1

HCID 57588245HCID 57588245, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (23) (0.065 mol) in THF (250 ml) was treated with liquid NH3 in an autoclave at 125° C. during 16 hours. The reaction mixture was filtered and the filtrate was evaporated. The residue was partitioned between a 5% aqueous NaOH solution and DCM. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 16 g of 1,1-dimethylethyl (trans)4-(aminomethyl)-3-methoxy-1-piperidinecarboxylate (intermediate (24).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was partitioned between a 5% aqueous NaOH solution and DCM
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-bcc52f18ea254431843935fb7c8bcc82
Source dataset
uspto-grants-2009_03
Patent number
US07498347B2

Reaction notes

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