Acetic Acid → 1-(10,10-Dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-2,2,2-trifluoro-ethanone acetic acid salt

HRID 712951Notes

Reaction equation

HRID 712951 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].C([N:12]1[CH2:28][C:27]([CH3:30])([CH3:29])[O:26][C:14]2([CH2:19][CH2:18][N:17]([C:20](=[O:25])[C:21]([F:24])([F:23])[F:22])[CH2:16][CH2:15]2)[CH2:13]1)C1C=CC=CC=1.Cl.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[C:1]([OH:4])(=[O:3])[CH3:2].[CH3:29][C:27]1([CH3:30])[O:26][C:14]2([CH2:19][CH2:18][N:17]([C:20](=[O:25])[C:21]([F:22])([F:23])[F:24])[CH2:16][CH2:15]2)[CH2:13][NH:12][CH2:28]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 866724521-(8-Benzyl-10,10-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-2,2,2-trifluoro-ethanoneHCID 178418361HCID 178418361, compound

Product 1

HCID 866724531-(10,10-Dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-2,2,2-trifluoro-ethanone acetic acid salt

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of acetic acid (100 μL, 1.76 mmol), Pd(OH)2 (11 mg, 0.02 mmol), 1-(8-benzyl-10,10-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-2,2,2-trifluoro-ethanone (80 mg, 0.22 mmol), HCl (108 μL of 4 M in dioxane, 0.43 mmol) and ethanol (2 mL) was treated to an atmosphere of hydrogen at 85 psi for 3 days. The reaction mixture was filtered and the catalyst was washed with methanol, then concentrated in vacuo to give 1-(10,10-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-2,2,2-trifluoro-ethanone acetic acid salt as a yellow solid. ESI-MS m/z calc. 280.1. found 281.5 (M+1)+; Retention time: 0.91 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe catalyst was washed with methanol
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d4910923c45c400ab8eafc6985b069c7
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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