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

HRID 1689419Notes

Reaction equation

HRID 1689419 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-57ecbb36aad545769415df00790a2bc2
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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