Sodium Hydroxide → HCID 59733746, compound

HRID 132107Notes

Reaction equation

HRID 132107 reaction equation
Cl.[C:2]([C:6]1[CH:7]=[C:8]([C:12]2([NH2:22])[CH2:21][CH2:20][C:15]3(OCC[O:16]3)[CH2:14][CH2:13]2)[CH:9]=[CH:10][CH:11]=1)([CH3:5])([CH3:4])[CH3:3].[OH-].[Na+]>C(O)(=O)C.O>[NH2:22][C:12]1([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[CH:7]=2)[CH2:13][CH2:14][C:15](=[O:16])[CH2:20][CH2:21]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 68977302HCID 68977302, compound

Product 1

HCID 59733746HCID 59733746, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 8-(3-tert-Butyl-phenyl)-1,4-dioxa-spiro[4.5]dec-8-ylamine hydrochloride (337 mg, 1.03 mmol) in glacial acetic acid (9 mL) and water (4 mL) was heated to 75° C. for 21 h, whereupon the reaction was deemed complete by HPLC analysis. The reaction mixture was basified with 2.5 N NaOH solution, then extracted with ethyl acetate (3×25 mL). The combined organic layers were washed (brine), dried (Na2SO4), filtered and concentrated under reduced pressure. Material was pure by HPLC/MS: retention time=1.18 min, method [7]; mass spec (ESI) 246 (MH+, 33), 229 (M−NH2+, 100), 228 (28), 173 (47).

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. washThe combined organic layers were washed (brine)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f47a763c48f34693ae19a479f2c6378d
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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