Water → rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

HRID 81349Notes

Reaction equation

HRID 81349 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@@H:10]1[OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:28]OS(OC)(=O)=O.O>C1COCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:11][C@H:10]1[O:25][CH3:28])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 58303445Phenylmethyl (3S,4S)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-hydroxy-1-piperidinecarboxylate

Product 1

HCID 58522570rel-Phenylmethyl (3R,4R)-4-[[(1,1-dimethylethoxy)carbonyl]amino]-3-methoxy-1-piperidinecarboxylate

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

benzyl (3S,4S)-4-tert-butoxycarbonylamino-3-hydroxy-piperidine-1-carboxylate (5.00 g) is dissolved in THF (6 mL) and combined with 30 mL aqueous, semiconcentrated NaOH solution, benzyltriethylammonium chloride as well as dimethylsulphate (2.26 mL). After 22 h H2O (200 mL) is added and the mixture is extracted with EtOAc (150 mL). The organic phase is dried on magnesium sulphate, filtered off from the desiccant and the solvent is eliminated in vacuo. Purification is carried out using a silica gel column (cHex/EtOAc 65/35).

Workup

  1. extractionthe mixture is extracted with EtOAc (150 mL)
  2. customThe organic phase is dried on magnesium sulphate
  3. filtrationfiltered off from the desiccant and the solvent
  4. customPurification

Sources & evidence

ORD record
ord-4ced7a16961f4e099f0f5614f0aa8edc
Source dataset
uspto-grants-2014_09
Patent number
US08846689B2

Reaction notes

Loading…