Ammonia → HCID 70169580, compound

HRID 1870228Notes

Reaction equation

HRID 1870228 reaction equation
[NH2:1][C:2]1[C:25]([Cl:26])=[CH:24][C:5]([C:6]([O:8][CH2:9][C@H:10]2[CH2:15][CH2:14][N:13](C(OC(C)(C)C)=O)[CH2:12][C@H:11]2[OH:23])=[O:7])=[C:4]([O:27][CH3:28])[CH:3]=1.Cl.CC(O)C.N>C1COCC1>[NH2:1][C:2]1[C:25]([Cl:26])=[CH:24][C:5]([C:6]([O:8][CH2:9][C@H:10]2[CH2:15][CH2:14][NH:13][CH2:12][C@H:11]2[OH:23])=[O:7])=[C:4]([O:27][CH3:28])[CH:3]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 86755578HCID 86755578, compound

Product 1

HCID 70169580HCID 70169580, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-1,1-dimethylethyl cis-4-[[(4-amino-5-chloro-2-methoxybenzoyl)oxy]-methyl]-3-hydroxy-1-piperidinecarboxylate (0.053 mol) in THF (250 ml) and a mixture of HCl and 2-propanol (25 ml) was stirred for 2 hours at room temperature, then for 10 minutes at 50° C., then cooled again to room temperature. The mixture was alkalinized with NH3. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 90/10). The pure fractions were collected and the solvent was evaporated, yielding 4.6 g (29%) (±) cis-(3-hydroxy-4-piperidinyl)methyl 4-amino-5-chloro-2-methoxybenzoate (interm. 6-a).

Workup

  1. waitfor 10 minutes at 50° C.
  2. temperaturecooled again to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 90/10)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a87ff8c71e9a46e08a1a0be5ad4099b2
Source dataset
uspto-grants-2000_08
Patent number
US06096761

Reaction notes

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