Water → HCID 68290887, compound

HRID 712952Notes

Reaction equation

HRID 712952 reaction equation
Cl.[CH2:2]([N:4]1[CH2:20][C:19]([CH3:22])([CH3:21])[O:18][C:6]2([CH2:11][CH2:10][N:9](C(=O)C(F)(F)F)[CH2:8][CH2:7]2)[CH2:5]1)[CH3:3].[OH-].[Li+].O>C1COCC1>[CH2:2]([N:4]1[CH2:5][C:6]2([CH2:11][CH2:10][NH:9][CH2:8][CH2:7]2)[O:18][C:19]([CH3:21])([CH3:22])[CH2:20]1)[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 88924193HCID 88924193, compound

Product 1

HCID 68290887HCID 68290887, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1-(8-ethyl-10,10-dimethyl-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl)-2,2,2-trifluoro-ethanone hydrochloride salt (47 mg, 0.14 mmol) and lithium hydroxide (10 mg, 0.42 mmol) was added water (0.15 mL) and THF (0.6 mL) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo, partitioned between DCM (10 mL)/1:1 brine:NH4OH (2 mL), extracted with DCM (5×10 mL), dried over MgSO4 and concentrated in vacuo to give 4-ethyl-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane (24 mg, 81%). ESI-MS m/z calc. 212.2. found 213.5 (M+1)+; Retention time: 0.19 minutes (3 min run).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between DCM (10 mL)/1
  3. extraction1 brine:NH4OH (2 mL), extracted with DCM (5×10 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ba02b63bf5e04bedac07cab0c4892522
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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