Carbon Dioxide → HCID 59383053, compound

HRID 1254396Notes

Reaction equation

HRID 1254396 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@:8]([C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH:5]=[CH:6][CH:7]=1.C([Li])(C)(C)C.CCCCC.[C:39](=[O:41])=[O:40].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:25]([O:24][C:22]([N:18]1[CH2:19][CH2:20][CH2:21][C@@H:16]([C@@:8]([C:4]2[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=2)[C:39]([OH:41])=[O:40])([OH:15])[CH2:9][CH2:10][CH2:11][CH2:12][O:13][CH3:14])[CH2:17]1)=[O:23])([CH3:28])([CH3:27])[CH3:26]

Participants

7

Reactant 5

HCID 280Carbon DioxideHCID 8003PentaneHCID 10340Sodium CarbonateHCID 59382958HCID 59382958, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 59383053HCID 59383053, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-tert-butyl 3-((S)-1-(3-bromophenyl)-1-hydroxy-5-methoxy-pentyl)piperidine-1-carboxylate (279.1 mg, 0.61 mmol) in THF (5 mL) at −70° C. was added t-butyllithium in pentane (1.7 M, 0.71 mL, 1.22 mmol) dropwise. When the addition was complete dried carbon dioxide was bubbled through the reaction system for 10 min, and completion of reaction was confirmed by LC-MS. The solution was warmed to rt, and sat'd aq Na2CO3 solution (5 mL) was added. The organic layer was separated, and washed once with 1 N NaOH (2 mL). The combined aqueous solutions were acidified with 1 N aq HCl and extracted with EtOAc (5×5 mL). The organic layer was dried over Na2SO4, and concentrated under vacuum to give 3-((S)-1-((R)-1-(tert-butoxycarbonyl)piperidin-3-yl)-1-hydroxy-5-methoxy-pentyl)benzoic acid (152.4 mg, 59%) as a white solid. MS m/z 422 (M+H+).

Workup

  1. additionWhen the addition
  2. customwas bubbled through the reaction system for 10 min
  3. customcompletion of reaction
  4. additionwas added
  5. customThe organic layer was separated
  6. washwashed once with 1 N NaOH (2 mL)
  7. extractionextracted with EtOAc (5×5 mL)
  8. dry with materialThe organic layer was dried over Na2SO4
  9. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-c6c0e1b0fad64531b9c7b37edb21c8c4
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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