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

HRID 1255347Notes

Reaction equation

HRID 1255347 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-d7a88822dae4476d8fb005ecced452f7
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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