Sodium Carbonate → 2-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-4-fluorophenyl)ethanol

HRID 446467Notes

Reaction equation

HRID 446467 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].FC(F)(F)C([N:11]1[CH2:16][C:15]2([CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[C:27]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:25][C:24]=3[F:32])[CH2:18][CH2:17]2)[O:14][CH2:13][CH2:12]1)=O>O.C(#N)C>[O:14]1[C:15]2([CH2:21][CH2:20][N:19]([CH2:22][C:23]3[CH:28]=[C:27]([CH2:29][CH2:30][OH:31])[CH:26]=[CH:25][C:24]=3[F:32])[CH2:18][CH2:17]2)[CH2:16][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 581685882,2,2-Trifluoro-1-(9-(2-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Product 1

HCID 581684902-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-4-fluorophenyl)ethanol

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

A solution of sodium carbonate (1.4 g) in water (40 mL) was added to a solution of 2,2,2-trifluoro-1-(9-(2-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone [Example 44, step b] (4.2 g) in acetonitrile (40 mL). The reaction mixture was stirred at 20° C. for 20 hours. The acetonitrile was removed under reduced pressure and the remaining aqueous solution was extracted with DCM (×9). The combined DCM extracts were dried, filtered and the solvent removed under reduced pressure to yield the subtitled compound. Yield 2.7 g.

Workup

  1. customThe acetonitrile was removed under reduced pressure
  2. extractionthe remaining aqueous solution was extracted with DCM (×9)
  3. dry with materialThe combined DCM extracts were dried
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-48bcf37cbd864fa58ac19310fec3729d
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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