Methanol → tert-Butyl 2-oxa-9-azaspiro[5.5]undecane-9-carboxylate

HRID 2213041Notes

Reaction equation

HRID 2213041 reaction equation
CCOC(/N=N/C(OCC)=O)=O.O[CH2:14][C:15]1([CH2:28][CH2:29][CH2:30][OH:31])[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO>O1CCCC1>[CH2:14]1[C:15]2([CH2:16][CH2:17][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:22])[CH2:19][CH2:20]2)[CH2:28][CH2:29][CH2:30][O:31]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776Triphenylphosphine2×HCID 5462977Diethyl azodicarboxylate2×HCID 21955378HCID 21955378, compound

Product 1

HCID 21955183tert-Butyl 2-oxa-9-azaspiro[5.5]undecane-9-carboxylateYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diethyl diazenedicarboxylate (390 μL, 2.46 mmol) was added to a solution of 1,1-dimethylethyl 4-(hydroxymethyl)-4-(3-hydroxypropyl)-1-piperidinecarboxylate (Description 137, 560 mg, 2.05 mmol) and triphenylphosphine (646 mg, 2.46 mmol) in tetrahydrofuran (10 mL) and the mixture was stirred at room temperature for 24 hours. Further triphenylphosphine (646 mg, 2.46 mmol) and diethyl diazenedicarboxylate (390 μL, 2.46 mmol) were added and the mixture was stirred at room temperature for 24 hours. Methanol (5 mL) was added and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (75:25), to give the title compound (78 mg, 15%). m/z (ES+) 256 (M+1).

Workup

  1. stirringthe mixture was stirred at room temperature for 24 hours
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue was purified by flash column chromatography on silica gel
  4. washeluting with isohexane/EtOAc (75:25)

Sources & evidence

ORD record
ord-2c152b735e8c4bc98df050dd5580b394
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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