Ammonia → 2-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenyl)ethanol

HRID 471189Notes

Reaction equation

HRID 471189 reaction equation
N.FC(F)(F)C([N:6]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][CH2:25][OH:26])[CH:19]=3)[CH2:13][CH2:12]2)[O:9][CH2:8][CH2:7]1)=O>CO>[O:9]1[C:10]2([CH2:12][CH2:13][N:14]([CH2:17][C:18]3[CH:19]=[C:20]([CH2:24][CH2:25][OH:26])[CH:21]=[CH:22][CH:23]=3)[CH2:15][CH2:16]2)[CH2:11][NH:6][CH2:7][CH2:8]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 579889742,2,2-Trifluoro-1-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone

Product 1

HCID 579893852-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

‘880’ Ammonia solution (5 mL) was added to a solution of 2,2,2-trifluoro-1-(9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone (example 12, step e) (2.02 g) in methanol (25 mL). The resulting mixture was stirred for 90 min and the solvent evaporated. The residue was purified by silica gel chromatography eluting with 94.5:5:0.5 to 89:10:1 DCM:methanol:‘880’ aqueous ammonia gradient. The fractions containing product were combined and evaporated to give the subtitled compound as a clear oil. Yield 1.44 g.

Workup

  1. customthe solvent evaporated
  2. customThe residue was purified by silica gel chromatography
  3. washeluting with 94.5:5:0.5 to 89:10:1 DCM
  4. additionThe fractions containing product
  5. customevaporated

Sources & evidence

ORD record
ord-63cc171aab18453dbb32f7593cb7f58a
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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