Water → 7-Boc-2-oxa-7-azaspiro[3.5]nonane

HRID 2213013Notes

Reaction equation

HRID 2213013 reaction equation
O[CH2:2][C:3]1([CH2:16][O:17]S(C)(=O)=O)[CH2:8][CH2:7][N:6]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:5][CH2:4]1.[H-].[Na+].O>O1CCCC1>[CH2:2]1[C:3]2([CH2:4][CH2:5][N:6]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:7][CH2:8]2)[CH2:16][O:17]1

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 179799801,1-Dimethylethyl 4-Hydroxymethyl-4-methanesulfonyloxymethyl-1-piperidinecarboxylate

Product 1

HCID 219552107-Boc-2-oxa-7-azaspiro[3.5]nonaneYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1,1-dimethylethyl 4-hydroxymethyl-4-methanesulfonyloxymethyl-1-piperidinecarboxylate (Description 68, 3 g, 9.3 mmol) in tetrahydrofuran (200 mL) was added dropwise to a stirred suspension of sodium hydride (60% dispersion in mineral oil, 2.2 g, 55.8 mmol) in tetrahydrofuran (50 mL) and the mixture was stirred at room temperature for 72 hours. Water (5 mL) was added and the mixture was extracted with ethyl acetate (3×400 mL). The combined organic fractions were dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (80:20 increasing to 50:50), to give the title compound (1.5 g, 71%). m/z (ES+) 228 (M+1).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (3×400 mL)
  2. dry with materialThe combined organic fractions were dried (MgSO4)
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washeluting with isohexane/EtOAc (80:20 increasing to 50:50)

Sources & evidence

ORD record
ord-1c03e7283f814aee95a43dc7a3f03250
Source dataset
uspto-grants-2006_09
Patent number
US07105507B2

Reaction notes

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