Citric Acid → 1,2-dibenzyl 1-tert.butyl 1-(hydroxymethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

HRID 1464366Notes

Reaction equation

HRID 1464366 reaction equation
B.C(C[C:5]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22])[C@H:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=O.C(O)(=O)C[C:40](CC(O)=O)(C(O)=O)[OH:41]>O1CCCC1>[OH:41][CH2:40][C:5]([C:31]([O:33][C:34]([CH3:37])([CH3:35])[CH3:36])=[O:32])([C:21]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22])[C@H:6]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[CH2:7][CH:8]([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 6331BoraneHCID 867477791,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

Product 1

HCID 678262291,2-dibenzyl 1-tert.butyl 1-(hydroxymethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

8.2 ml of a 1M solution of borane in tetrahydrofuran was added to a solution of 4.055 g of 1,2-dibenzyl 1-tert.butyl 1-(formylmethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in 40 ml of dry tetrahydrofuran. After stirring for 5 minutes, the mixture was acidified with 5% aqueous citric acid solution and was extracted twice with ethyl acetate. The combined extracts were washed with saturated sodium chloride solution, dried over anhydrous magnesium sulfate and evaporate. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate for the elution. There was obtained 2.518 g of 1,2-dibenzyl 1-tert.butyl 1-(hydroxymethyl)-4-methyl-1,1,2(R)-pentanetricarboxylate in the form of a colorless oil.

Workup

  1. extractionwas extracted twice with ethyl acetate
  2. washThe combined extracts were washed with saturated sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporate
  5. customThe residue was purified by flash chromatography on silica gel
  6. washfor the elution

Sources & evidence

ORD record
ord-5b4ba37ba90b492a9241977792604083
Source dataset
uspto-grants-1994_04
Patent number
US05304549

Reaction notes

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