Benzylamine → HCID 53824934, compound

HRID 1869237Notes

Reaction equation

HRID 1869237 reaction equation
[OH:1][C@@H:2]1[C@@H:7]([CH2:8]OS(C2C=CC(C)=CC=2)(=O)=O)[CH2:6][CH2:5][N:4]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:3]1.[CH2:27]([NH2:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C1COCC1>[OH:1][C@@H:2]1[C@@H:7]([CH2:8][NH:34][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:6][CH2:5][N:4]([C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH2:3]1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 11200002HCID 11200002, compound

Product 1

HCID 53824934HCID 53824934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1,1-dimethylethyl(3R-trans)-3-hydroxy-4-[[(4-methylphenyl)-sulfonyl]oxymethyl]-1-piperidinecarboxylate [described in WO-00/37461 as intermediate (1-c-I)] (0.03 mol) and benzylamine (0.1 mol) in THF (250 ml) was stirred for 16 hours at 125° C. (autoclave). The reaction mixture was cooled and the solvent was evaporated. The residue was partitioned between DCM and an aqueous K2CO3 solution. The organic layer was separated, dried, filtered and the solvent was evaporated. The residue was crystallized from DIPE, yielding 5.3 g of 1,1-dimethyl-ethyl (3R-trans)-3-hydroxy-4-[[(phenylmethyl)amino]methyl]-1-piperidinecarboxylate (intermediate 60) ([α]20,D=−68.65° (c=23.16 mg/S ml in CH3OH); mp. 91° C.).

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between DCM
  4. customThe organic layer was separated
  5. customdried
  6. filtrationfiltered
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from DIPE

Sources & evidence

ORD record
ord-8ff82d1b6535473093f88ad7e56ef66f
Source dataset
uspto-grants-2009_12
Patent number
US07638535B2

Reaction notes

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