Sodium Methoxide → {1-[2-((3S,4S)-4-Hydroxy-3-methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

HRID 1928985Notes

Reaction equation

HRID 1928985 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][C@H:20]([O:23]C(=O)C(C)(C)C)[C@@H:19]([CH3:30])[CH2:18]2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][C@H:20]([OH:23])[C@@H:19]([CH3:30])[CH2:18]2)[CH2:11][CH2:10]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 668413002,2-Dimethyl-propionic acid (3S,4S)-1-[2-(4-tert-butoxycarbonylamino-piperidin-1-yl)-ethyl]-3-methyl-piperidin-4-yl ester

Product 1

HCID 67523806{1-[2-((3S,4S)-4-Hydroxy-3-methyl-piperidin-1-yl)-ethyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

Procedure

Crude 15 (8.2 g, 19.27 mmol) is treated with NaOMe (0.5M in methanol, 77 ml, 38.5 mmol) and heated under reflux for 24 hours. The solvent is then evaporated, the residue taken up in DCM and extracted with 1N-NaOH and brine. Drying and evaporation gave a brown oil which is purified by chromatography on silicagel using DCM (saturated with ammonia) and MeOH (from 1% to 5%).

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent is then evaporated
  4. extractionextracted with 1N-NaOH and brine
  5. customDrying
  6. customevaporation
  7. customgave a brown oil which
  8. customis purified by chromatography on silicagel

Sources & evidence

ORD record
ord-293744f074ca40c19243d415879dcdc0
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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