Hydrochloric Acid → HCID 59619438, compound

HRID 1367484Notes

Reaction equation

HRID 1367484 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2].[BH4-].[Na+].Cl.[Cl-].[Na+]>O1CCCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([OH:11])[CH2:8][C@H:7]1[C:12]([OH:14])=[O:13])=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 59619308HCID 59619308, compound

Product 1

HCID 59619438HCID 59619438, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cold (ice bath solution of (1R,2R)-4-Oxo-cyclopentane-1,2-dicarboxylic acid monoethyl ester (3.0 g) in tetrahydrofuran (30 mL) was added sodium borohydride (737 mg) in several portions over 5.5 h. After 6.5 h, hydrochloric acid (1N, 40 mL) then sodium chloride (8 g) were added to the reaction mixture. After 30 min, the reaction mixture was extracted with ethyl acetate. The organic layers were dried over sodium sulfate and concentrated in vacuo to afford the title compound (3.2 g, 95%) as colorless oil, used in the next step without further purification. MS (EI): 201.2 (M−H)−.

Workup

  1. waitAfter 30 min
  2. extractionthe reaction mixture was extracted with ethyl acetate
  3. dry with materialThe organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4c5f1116e6ec4f57800abde93f4490db
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

Loading…