Ammonium formate → HCID 68291515, compound

HRID 73034Notes

Reaction equation

HRID 73034 reaction equation
C([N:8]1[CH2:31][CH:30]([C:32]([OH:35])([CH3:34])[CH3:33])[O:29][C:10]2([CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[C:20]([CH3:28])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[CH2:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:35][C:32]([CH:30]1[CH2:31][NH:8][CH2:9][C:10]2([CH2:15][CH2:14][N:13]([C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:26])[CH3:27])=[C:20]([CH3:28])[CH:19]=3)=[O:17])[CH2:12][CH2:11]2)[O:29]1)([CH3:34])[CH3:33]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68310777[8-Benzyl-10-(1-hydroxy-1-methyl-ethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

Product 1

HCID 68291515HCID 68291515, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

[8-Benzyl-10-(1-hydroxy-1-methyl-ethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (75 mg, 0.16 mmol) was dissolved in ethanol (3 mL) and Pd (8 mg, 0.008 mmol) and ammonium formate (50 mg, 0.80 mmol) were added and the reaction mixture was heated at 75° C. for 30 minutes. The reaction mixture was filtered, concentrated in vacuo, diluted with ethyl acetate, washed with 3M NaOH, dried over MgSO4, filtered and concentrated in vacuo to give (2-(2-hydroxypropan-2-yl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)(4-isopropoxy-3-methylphenyl)methanone (60 mg, 94%). ESI-MS m/z calc. 390.3. Found 391.5 (M+1)+; Retention time: 1.27 minutes (3 min run).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo
  3. additiondiluted with ethyl acetate
  4. washwashed with 3M NaOH
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26cbf3f76d8a4674a7f07188ae85b1d0
Source dataset
uspto-grants-2014_09
Patent number
US08828996B2

Reaction notes

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