Azetidine → HCID 66850495, compound

HRID 453905Notes

Reaction equation

HRID 453905 reaction equation
O=[C:2]1[CH2:19][CH2:18][C:5]2([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]2)[CH2:4][CH2:3]1.[NH:20]1[CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[N:20]1([CH:2]2[CH2:19][CH2:18][C:5]3([CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]3)[CH2:4][CH2:3]2)[CH2:23][CH2:22][CH2:21]1

Participants

6

Reactant 4

HCID 10422AzetidineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 51072194tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate

Product 1

HCID 66850495HCID 66850495, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

tert-Butyl 9-oxo-3-azaspiro[5.5]undecane-3-carboxylate (stage (iv) Amine-F43) (1 g, 3.74 mmol) and azetidine (0.25 ml, 3.74 mmol) were placed in 1,2-dichloroethane (15 ml), and sodium triacetoxyborohydride (1.1 g, 5.23 mmol) was added. The reaction mixture was stirred for 3 d at room temperature, and then saturated sodium hydrogen carbonate solution was added. After phase separation, the aqueous phase was extracted with dichloromethane (2×). The combined organic phases were washed with saturated sodium chloride solution (1×), dried over magnesium sulfate and concentrated under vacuum. The crude product was purified by column chromatography (silica gel, ethyl acetate/methanol/ammonia (25% aq.), 100:10:1). Yield: 1 g (89%)

Workup

  1. customAfter phase separation
  2. extractionthe aqueous phase was extracted with dichloromethane (2×)
  3. washThe combined organic phases were washed with saturated sodium chloride solution (1×)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe crude product was purified by column chromatography (silica gel, ethyl acetate/methanol/ammonia (25% aq.), 100:10:1)

Sources & evidence

ORD record
ord-c91f793d3821475faf0137e50c819b50
Source dataset
uspto-grants-2013_07
Patent number
US08492559B2

Reaction notes

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