Ammonia → 2-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-5-fluorophenyl)ethanol

HRID 471108Notes

Reaction equation

HRID 471108 reaction equation
N.[F:2][C:3]1[CH:4]=[C:5]([CH:31]=[C:32]([CH2:34][CH2:35][OH:36])[CH:33]=1)[CH2:6][N:7]1[CH2:30][CH2:29][C:10]2([O:15][CH2:14][CH2:13][N:12](C(C3N=C(C4C=CC=CC=4)SC=3)=O)[CH2:11]2)[CH2:9][CH2:8]1>CO>[O:15]1[C:10]2([CH2:29][CH2:30][N:7]([CH2:6][C:5]3[CH:31]=[C:32]([CH2:34][CH2:35][OH:36])[CH:33]=[C:3]([F:2])[CH:4]=3)[CH2:8][CH2:9]2)[CH2:11][NH:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 57989277(9-(3-Fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-phenylthiazol-4-yl)methanone

Product 1

HCID 579889902-(3-(1-Oxa-4,9-diazaspiro[5.5]undecan-9-ylmethyl)-5-fluorophenyl)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-fluoro-5-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)ethanone (example 41, step d) (2.2 g) in methanol (25 mL). The resulting mixture was stirred for 90 min and the solvent evaporated. The residue was azeotroped three times with acetonitrile and concentrated to give the subtitled compound as a clear gum. Yield 1.96 g.

Workup

  1. customthe solvent evaporated
  2. customThe residue was azeotroped three times with acetonitrile
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2960abd10b234dfdbce2f3746f1af1c3
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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