HCID 59382960, compound → HCID 67191356, compound

HRID 1254267Notes

Reaction equation

HRID 1254267 reaction equation
[C:1]1([CH3:29])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1)=[O:15]>C1COCC1>[C:1]1([CH3:29])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C@:14]([C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:28])[CH3:27])=[O:23])[CH2:17]1)([OH:15])[CH2:5][CH2:6][CH2:1][CH2:2][O:7][CH3:8]

Participants

3

Reactant 1

HCID 59382960HCID 59382960, compound

Product 1

HCID 67191356HCID 67191356, compoundYield 165.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 1000-mL, three-necked flask was charged with the (2-(o-tolyloxy)phenyl)((R)-1-(tert-butoxycarbonyl)piperidin-3-yl)methanone (20 g, 0.05 mol) and THF (250 mL). The flask was evacuated and refilled with N2, the mixture was cooled with a dry ice-acetone bath and the Grignard reagent was added dropwise. The mixture was allowed to warm slowly to rt and stirred overnight. After quenching with sat'd aq NH4Cl (500 mL), the mixture was extracted with EtOAc (3×150 mL) and the combined organic layers were dried over Na2SO4. The solvent was removed and the crude product was purified by flash column chromatography to afford the (R)-tert-butyl 3-((S)-1-(2-(o-tolyloxy)phenyl)-1-hydroxy-5-methoxypentyl)piperidine-1-carboxylate (20 g, 83%).

Workup

  1. customThe flask was evacuated
  2. additionrefilled with N2
  3. temperaturethe mixture was cooled with a dry ice-acetone bath
  4. additionthe Grignard reagent was added dropwise
  5. customAfter quenching with sat'd aq NH4Cl (500 mL)
  6. extractionthe mixture was extracted with EtOAc (3×150 mL)
  7. dry with materialthe combined organic layers were dried over Na2SO4
  8. customThe solvent was removed
  9. customthe crude product was purified by flash column chromatography

Sources & evidence

ORD record
ord-2d2c944bec1e49a999e08173c961a0dd
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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