Potassium tert-butoxide → 2-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-7-one

HRID 471039Notes

Reaction equation

HRID 471039 reaction equation
[CH:1]([N:14]1[CH2:17][C:16]([CH2:19][NH:20][C:21](=[O:24])[CH2:22]Cl)([OH:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+]>C1COCC1>[CH:1]([N:14]1[CH2:17][C:16]2([CH2:19][NH:20][C:21](=[O:24])[CH2:22][O:18]2)[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 57988954N-((1-Benzhydryl-3-hydroxyazetidin-3-yl)methyl)-2-chloroacetamide

Product 1

HCID 579892642-Benzhydryl-5-oxa-2,8-diazaspiro[3.5]nonan-7-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
75 °C

Procedure

N-((1-Benzhydryl-3-hydroxyazetidine-3-yl)methyl)-2-chloroacetamide (example 33, step d) (2.6 g) in THF (50 mL) was added dropwise over 90 minutes to a vigorously stirred solution at 75° C. of potassium tert-butoxide (1M in tert-butanol, 15.08 mL) and THF (150 mL) under nitrogen. After the addition was complete the mixture was stirred at 75° C. for 10 minutes and then cooled to room temperature. The solvents were removed under reduced pressure and the residue was partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent removed under reduced pressure to afford the subtitled compound. Yield 2.05 g.

Workup

  1. additionAfter the addition
  2. temperaturecooled to room temperature
  3. customThe solvents were removed under reduced pressure
  4. customthe residue was partitioned between ethyl acetate and brine
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-78d0e4ecea58406d8479592059c3a87b
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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