Citric Acid → HCID 131729683, compound

HRID 1920183Notes

Reaction equation

HRID 1920183 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:12][C@@H:11]([C:25](OC)=[O:26])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[Cl-].[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:10][C@@H:11]([CH2:25][OH:26])[CH2:12][N:13]([C:15]([O:17][CH2:18][C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)=[O:16])[CH2:14]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 95731685cis (+/-)-1-Benzyl 3-methyl 5-(tert-butoxycarbonylamino)piperidine-1,3-dicarboxylate

Product 1

HCID 131729683HCID 131729683, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of cis(+/−)-1-benzyl 3-methyl 5-(tert-butoxycarbonylamino)piperidine-1,3-dicarboxylate (1.0 eq.) in THF at a concentration of 0.08 M was cooled at 0° C. and then LiCl (2.3 eq.) and sodium borohydride (2.3 eq.) were added. After stirring for 20 hours as the reaction warmed to rt, the pH was adjusted with 1M citric acid to pH 4-5. After removal of the volatiles in vacuo, the product was extracted in dichloromethane, washed with H2O and brine, dried over MgSO4. Upon filtering and removal of the volatiles in vacuo, cis(+/−)-benzyl 3-(tert-butoxycarbonylamino)-5-(hydroxymethyl)piperidine-1-carboxylate was obtained as a white foamy solid. LCMS (m/z): 265.0 (MH-Boc+); LC Rt=3.37 min.

Workup

  1. customAfter removal of the volatiles in vacuo
  2. extractionthe product was extracted in dichloromethane
  3. washwashed with H2O and brine
  4. dry with materialdried over MgSO4
  5. filtrationUpon filtering
  6. customremoval of the volatiles in vacuo

Sources & evidence

ORD record
ord-13fede006101488fab500bad3c572186
Source dataset
uspto-grants-2012_05
Patent number
US08168794B2

Reaction notes

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