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

HRID 2267712Notes

Reaction equation

HRID 2267712 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:15][C@@H:16]([N:18]2[CH2:23][CH2:22][C@H:21]([O:24]C(=O)C(C)(C)C)[C@@H:20]([CH3:31])[CH2:19]2)[CH3:17])[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][C@@H:16]([N:18]2[CH2:23][CH2:22][C@H:21]([OH:24])[C@@H:20]([CH3:31])[CH2:19]2)[CH3:17])[CH2:11][CH2:10]1)([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 10942334Sodium MethoxideHCID 668419902,2-Dimethyl-propionic acid (3S,4S)-1-[(S)-2-(4-tert-butoxycarbonylamino-piperidin-1-yl)-1-methyl-ethyl]-3-methyl-piperidin-4-yl ester

Product 1

HCID 66844927{1-[(S)-2-((3S,4S)-4-Hydroxy-3-methyl-piperidin-1-yl)-propyl]-piperidin-4-yl}-carbamic acid tert-butyl ester

Procedure

Ester 58 from above (1.7 g, 3.52 mmol) is treated with NaOMe (0.5M in methanol, 21 ml, 10.5 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. After drying and evaporation the crued is purified by chromatography on silicagel using DCM (saturated with ammonia) and MeOH (from 1% to 3%) to give a white powder.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 24 hours
  3. customThe solvent is then evaporated
  4. extractionextracted with 1N—NaOH and brine
  5. customAfter drying
  6. customevaporation the
  7. customcrued is purified by chromatography on silicagel
  8. customto give a white powder

Sources & evidence

ORD record
ord-5b7b504989be4629af1da1dfdfacfc89
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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