Sodium hydride → HCID 66874260, compound

HRID 249896Notes

Reaction equation

HRID 249896 reaction equation
[CH2:1]1[C:5]2([CH2:10][N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:8][CH2:7][NH:6]2)[CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:21]1[O:22][C:23]2[C:24](=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:28][CH:29]=2)[N:25]=1>COCCOC>[C:14]([O:13][C:11]([N:9]1[CH2:10][C:5]2([CH2:1][CH2:2][CH2:3][CH2:4]2)[N:6]([C:21]2[O:22][C:23]3[C:24](=[C:26]([C:30]([O:32][CH3:33])=[O:31])[CH:27]=[CH:28][CH:29]=3)[N:25]=2)[CH2:7][CH2:8]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 56924368Methyl 2-chlorobenzo[d]oxazole-4-carboxylateHCID 668742416,9-DIAZA-SPIRO[4.5]DECANE-9-CARBOXYLIC ACID TERT-BUTYL ESTER

Product 1

HCID 66874260HCID 66874260, compoundYield 18.5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of tert-butyl 6,9-diazaspiro[4.5]decane-9-carboxylate (192 mg, 0.80 mmol) in DME (10 mL) was added NaH (60%, 96 mg, 2.4 mmol). The reaction mixture was stirred at room temperature for 10 min, followed by addition of methyl 2-chlorobenzoxazole-4-carboxylate (186 mg, 0.88 mmol). The reaction mixture was stirred at room temperature for 20 h. The reaction was quenched by adding 5 mL of H2O and extracted with EtOAc (2×30 mL). The organic layer was washed by brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, 50-100% chloroform in hexane) to afford methyl 2-(9-(tert-butoxycarbonyl)-6,9-diazaspiro[4.5]decan-6-yl)benzoxazole-4-carboxylate (61.4 mg, 18.5%) as yellow oil. MS consistent.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 20 h
  2. customThe reaction was quenched
  3. additionby adding 5 mL of H2O
  4. extractionextracted with EtOAc (2×30 mL)
  5. washThe organic layer was washed by brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue was purified by column chromatography (silica gel, 50-100% chloroform in hexane)

Sources & evidence

ORD record
ord-aee76fbec79240b3a3903430a7275fb4
Source dataset
uspto-grants-2011_01
Patent number
US07863271B2

Reaction notes

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