3-Aminoazetidine, 3-BOC protected → [1-(4-Benzo[1,3]dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-yl]-carbamic acid tert-butyl ester

HRID 1893218Notes

Reaction equation

HRID 1893218 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH2:15][CH2:14][C:13](=O)[CH2:12][CH:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:17]([O:21][C:22](=[O:28])[NH:23][CH:24]1[CH2:27][NH:26][CH2:25]1)([CH3:20])([CH3:19])[CH3:18].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:17]([O:21][C:22](=[O:28])[NH:23][CH:24]1[CH2:27][N:26]([CH:13]2[CH2:14][CH2:15][C:10]([C:8]3[CH:7]=[CH:6][C:5]4[O:1][CH2:2][O:3][C:4]=4[CH:9]=3)=[CH:11][CH2:12]2)[CH2:25]1)([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 15194053-Aminoazetidine, 3-BOC protectedHCID 5049666Sodium triacetoxyborohydrideHCID 595419144-(Benzo[D][1,3]dioxol-5-YL)cyclohex-3-enone

Product 1

HCID 59541968[1-(4-Benzo[1,3]dioxol-5-yl-cyclohex-3-enyl)-azetidin-3-yl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-benzo[1,3]dioxol-5-yl-cyclohex-3-enone (as prepared in the previous step, 680 mg, 3.15 mmol) and azetidin-3-yl-carbamic acid tert-butyl ester (BetaPharma, 542 mg, 3.15 mmol) in DCM (10 mL) was treated with NaBH(OAc)3 (Aldrich, 2.0 g, 9.45 mmol) at room temperature. The reaction was stirred for 4 hours and quenched with saturated sodium bicarbonate. The organic layer was separated and the aqueous layer was extracted 3 times with DCM. The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated to give the crude product, which was then purified by a CombiFlash® system using hexanes and ethyl acetate as eluent (from pure hexanes to pure ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customquenched with saturated sodium bicarbonate
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted 3 times with DCM
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give the crude product, which
  8. customwas then purified by a CombiFlash® system

Sources & evidence

ORD record
ord-39770de8faf24be186483d6f207fced0
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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