Sodium Bicarbonate → (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one

HRID 1719337Notes

Reaction equation

HRID 1719337 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:15]([CH2:16][CH:17](OC)[O:18]C)[NH:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.Cl>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[C@@H:15]([CH2:16][CH2:17][OH:18])[NH:14][C:13]1=[O:22])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 54521889(3R,4R)-3-benzyloxycarbonylamino-4-(2,2-dimethoxyethyl)azetidin-2-one

Product 1

HCID 13744723(3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-oneYield 63.6%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3R,4R)-3-(benzyloxycarbonylamino)-4-(2,2-dimethoxyethyl)azetidin-2-one (1.014 g) in tetrahydrofuran (15 ml) were added portionwise a solution of sodium cyanoborohydride (460 mg) in tetrahydrofuran (2.30 ml) and 2N hydrochloric acid (7.5 ml) at ambient temperature during a period of 90 minutes. The solution was adjusted to pH 7 with saturated aqueous sodium hydrogen carbonate and concentrated in vacuo. The concentrate was acidified to pH 4 with 2N hydrochloric acid, saturated with sodium chloride and extracted four times with chloroform. The combined extracts were dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (15 g, eluting with 3-10% methanol in dichloromethane) to give a crystalline solid, which was washed with ether and collected by filtration to give 553 mg of (3R,4R)-3-benzyloxycarbonylamino-4-(2-hydroxyethyl)azetidin-2-one.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted four times with chloroform
  3. dry with materialThe combined extracts were dried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed on silica gel (15 g, eluting with 3-10% methanol in dichloromethane)
  6. customto give a crystalline solid, which
  7. washwas washed with ether
  8. filtrationcollected by filtration

Sources & evidence

ORD record
ord-33a0caffd4604d129dee1910ad903270
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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