Toluene → 2-(3-((2,2-Dimethyl-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol

HRID 471284Notes

Reaction equation

HRID 471284 reaction equation
FC(F)(F)C(O)=O.[OH:8][CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][CH:37]=1)[CH2:14][N:15]1[CH2:34][CH2:33][C:18]2([O:23][C:22]([CH3:25])([CH3:24])[CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]2)[CH2:17][CH2:16]1.C1(C)C=CC=CC=1>C(Cl)Cl>[CH3:24][C:22]1([CH3:25])[CH2:21][NH:20][CH2:19][C:18]2([CH2:33][CH2:34][N:15]([CH2:14][C:13]3[CH:12]=[C:11]([CH2:10][CH2:9][OH:8])[CH:37]=[CH:36][CH:35]=3)[CH2:16][CH2:17]2)[O:23]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989267tert-Butyl 9-(3-(2-hydroxyethyl)benzyl)-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate

Product 1

HCID 579890912-(3-((2,2-Dimethyl-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
20 °C

Procedure

Trifluoroacetic acid (5 mL) was added to a solution of tert-butyl 9-(3-(2-hydroxyethyl)benzyl)-2,2-dimethyl-1-oxa-4,9-diazaspiro[5.5]undecane-4-carboxylate (Example 271, step d) (0.78 g) in DCM (20 mL) and the reaction mixture allowed to stand for 30 minutes at 20° C. Toluene (40 mL) was added and the solvents evaporated under reduced pressure, the residue was azeotroped with acetonitrile (×2). The residue was dissolved in water (30 mL) and washed with ethyl acetate, the aqueous layer was basified by addition of solid sodium carbonate and stirred for 30 minutes at 20° C. The aqueous mixture was then extracted with DCM (×6), the combined DCM layers were dried over sodium sulphate, filtered and the solvent evaporated under reduced pressure to afford the subtitled compound. Yield 0.4 g.

Workup

  1. customthe solvents evaporated under reduced pressure
  2. customthe residue was azeotroped with acetonitrile (×2)
  3. dissolutionThe residue was dissolved in water (30 mL)
  4. washwashed with ethyl acetate
  5. additionthe aqueous layer was basified by addition of solid sodium carbonate
  6. extractionThe aqueous mixture was then extracted with DCM (×6)
  7. dry with materialthe combined DCM layers were dried over sodium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-3d3f0af7c18042db81cdd37143a2ef63
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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