Potassium Carbonate → HCID 94411105, compound

HRID 2275021Notes

Reaction equation

HRID 2275021 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:15][C@H:16]1[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18][C@H:17]1[NH:32][C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])(=O)C1C=CC=CC=1>O.C(O)C>[C:36]([O:35][C:33]([NH:32][C@H:17]1[C@@H:16]([OH:15])[CH2:21][CH2:20][N:19]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[CH2:18]1)=[O:34])([CH3:39])([CH3:37])[CH3:38]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 131733418HCID 131733418, compound

Product 1

HCID 94411105HCID 94411105, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of potassium carbonate (3.70 g, 26.8 mmol) in water (80 mL) was added to a solution of cis-benzyl 4-(benzoyloxy)-3-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate (8.11 g, 17.84 mmol) in ethanol (160 mL) and the mixture was stirred at 70° C. for 20 h. The reaction mixture was concentrated in vacuo to ⅓rd volume and the resultant suspension was diluted with water (50 mL) and extracted using DCM (3×70 mL). The collected organics were combined and dried (Na2SO4) and concentrated in vacuo to afford the crude product as a colourless oil. The crude product was then purified by column chromatography on a silica cartridge (340 g) using a 0-100% ethyl acetate/cyclohexane gradient. The appropriate fractions were combined and evaporated in vacuo to give the required product cis-benzyl 3-((tert-butoxycarbonyl)amino)-4-hydroxypiperidine-1-carboxylate (5.54 g, 15.81 mmol, 89% yield) as a white foam.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe resultant suspension was diluted with water (50 mL)
  3. extractionextracted
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product as a colourless oil
  7. customThe crude product was then purified by column chromatography on a silica cartridge (340 g)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-be048a663e714785855c14d62f5df975
Source dataset
uspto-grants-2015_09
Patent number
US09127003B2

Reaction notes

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