(9-(2-(4-(Hydroxymethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone → 4-(2-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzaldehyde

HRID 1689185Notes

Reaction equation

HRID 1689185 reaction equation
[OH:1][CH2:2][C:3]1[CH:30]=[CH:29][C:6]([O:7][CH2:8][CH2:9][N:10]2[CH2:28][CH2:27][C:13]3([O:18][CH2:17][CH2:16][N:15]([C:19]([C:21]4[N:22]=[C:23]([CH3:26])[S:24][CH:25]=4)=[O:20])[CH2:14]3)[CH2:12][CH2:11]2)=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:26][C:23]1[S:24][CH:25]=[C:21]([C:19]([N:15]2[CH2:14][C:13]3([CH2:27][CH2:28][N:10]([CH2:9][CH2:8][O:7][C:6]4[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:30][CH:29]=4)[CH2:11][CH2:12]3)[O:18][CH2:17][CH2:16]2)=[O:20])[N:22]=1

Participants

4

Reactant 1

HCID 46240301(9-(2-(4-(Hydroxymethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 579889414-(2-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethoxy)benzaldehyde

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

Manganese dioxide (0.65 g) was added to a solution of (9-(2-(4-(hydroxymethyl)phenoxy)ethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (0.32 g) (example 1, step i) in DCM (20 mL) and the resulting black suspension heated under reflux for 1 h. After cooling the reaction mixture was passed through a pad of Celite. The pad was washed with DCM (2×30 mL) and the combined filtrate and washings evaporated in vacuo to give the subtitled compound as a gum.

Workup

  1. temperaturethe resulting black suspension heated
  2. temperatureunder reflux for 1 h
  3. temperatureAfter cooling the reaction mixture
  4. washThe pad was washed with DCM (2×30 mL)
  5. customthe combined filtrate and washings evaporated in vacuo

Sources & evidence

ORD record
ord-ee69bf4d03b14e8e9568dfb3df830000
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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