Acetic Acid → HCID 22975787, compound

HRID 2120961Notes

Reaction equation

HRID 2120961 reaction equation
C1(C[N:8]2[CH2:26][CH2:25][C:11]3([CH2:16][CH2:15][N:14]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13][CH2:12]3)[CH2:10][CH2:9]2)C=CC=CC=1.C(O)(=O)C>C(O)C>[CH2:16]1[C:11]2([CH2:25][CH2:26][NH:8][CH2:9][CH2:10]2)[CH2:12][CH2:13][N:14]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:15]1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 229758051,1-Dimethylethyl 9-(phenylmethyl)-3,9-diazaspiro[5.5]undecane-3-acetate

Product 1

HCID 22975787HCID 22975787, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 9.3 g (25.9 mmol) of the compound from Step E in 400 ml dry ethanol were added 1.5 ml acetic acid and 0.7 g Pd(II) hydroxide. The mixture was filled into an autoclave and hydrogenated at 50 atm and 50° C. for 18 h. The solvent was removed under reduced pressure, and the residue was stirred with saturated aqueous sodium bicarbonate solution. It was extracted five times with 100 ml tert.-butylmethylether followed by three extractions with 100 ml dichloromethane. The extracts were dried over sodium sulfate and concentrated in vacuo, separately. The first extract contained a mixture of compounds, whereas the pure title intermediate was obtaind from the following.

Workup

  1. additionThe mixture was filled into an autoclave and hydrogenated at 50 atm and 50° C. for 18 h
  2. customThe solvent was removed under reduced pressure
  3. extractionIt was extracted five times with 100 ml tert.-butylmethylether
  4. extractionfollowed by three extractions with 100 ml dichloromethane
  5. dry with materialThe extracts were dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. extractionThe first extract
  8. additiona mixture of compounds

Sources & evidence

ORD record
ord-9adb3ca50c984b41b0c6d7a3d2090a48
Source dataset
uspto-grants-2004_02
Patent number
US06693109B2

Reaction notes

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