Sodium Bicarbonate → Carbamic acid, N-[1-(tetrahydro-3-furanyl)-3-azetidinyl]-, 1,1-dimethylethyl ester

HRID 2167992Notes

Reaction equation

HRID 2167992 reaction equation
[NH:1]1[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]1.[O:13]1[CH2:17][CH2:16][C:15](=O)[CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCl>[O:13]1[CH2:17][CH2:16][CH:15]([N:1]2[CH2:4][CH:3]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:9])([CH3:11])[CH3:10])[CH2:2]2)[CH2:14]1

Participants

6

Reactant 4

HCID 516892Sodium BicarbonateHCID 5293923-OxotetrahydrofuranHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 67126577Carbamic acid, N-[1-(tetrahydro-3-furanyl)-3-azetidinyl]-, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tert-butyl azetidin-3-ylcarbamate (0.550 g), dihydrofuran-3(2H)-one (0.412 g) and sodium triacetoxyborohydride (1.015 g) were stirred together in dichloromethane (5 mL). After stirring overnight, the reaction was poured into saturated aqueous NaHCO3 solution (25 mL) and extracted with dichloromethane (50 mL). The organic layer was washed with brine (25 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography (GraceResolv 12 g) eluting with a gradient of 0.5% to 7.5% methanol/dichloromethane over 30 minutes gave tert-butyl 1-(tetrahydrofuran-3-yl)azetidin-3-ylcarbamate. The resulting material was treated with HCl/dioxane for 1 hour, and then concentrated to give the title compound.

Workup

  1. extractionextracted with dichloromethane (50 mL)
  2. washThe organic layer was washed with brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. washSilica gel chromatography (GraceResolv 12 g) eluting with a gradient of 0.5% to 7.5% methanol/dichloromethane over 30 minutes

Sources & evidence

ORD record
ord-2d3505c0059e4ef7abf43ef3c2b59754
Source dataset
uspto-grants-2015_06
Patent number
US09045475B2

Reaction notes

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