Potassium tert-butoxide → Tert-butyl 9-oxo-7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate

HRID 471209Notes

Reaction equation

HRID 471209 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][CH2:7][C:8]1([OH:21])[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]1)=[O:4].CC(C)([O-])C.[K+]>C1COCC1>[O:4]=[C:3]1[NH:5][CH2:6][CH2:7][C:8]2([CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[O:21][CH2:2]1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 57989111tert-Butyl 4-(2-(2-chloroacetamido)ethyl)-4-hydroxypiperidine-1-carboxylate

Product 1

HCID 57989131Tert-butyl 9-oxo-7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of tert-butyl 4-(2-(2-chloroacetamido)ethyl)-4-hydroxypiperidine-1-carboxylate (example 89, step c) (0.3 g) in dry THF (18 mL) was added dropwise over 6 hours to a refluxing mixture of potassium tert-butoxide (1M in tert-butanol, 3 mL) and dry THF (60 mL). At the end of the addition the mixture was heated at reflux for a further 15 minutes and then cooled to room temperature. The mixture was partitioned between ethyl acetate and brine. The organic layer was dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure. Tritruration with diethylether afforded the subtitled compound. Yield 0.117 g.

Workup

  1. additionAt the end of the addition the mixture
  2. temperaturewas heated
  3. temperatureat reflux for a further 15 minutes
  4. customThe mixture was partitioned between ethyl acetate and brine
  5. dry with materialThe organic layer was dried over sodium sulphate
  6. filtrationfiltered
  7. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-ecb46b3151fe4dbd81726689584d5120
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

Loading…