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

HRID 706902Notes

Reaction equation

HRID 706902 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-61d00c48f6f3411fa98ae7b0c139def9
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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