Trifluoroacetic acid → 2-(3-((4-(5-Methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)methyl)phenyl)acetaldehyde

HRID 470980Notes

Reaction equation

HRID 470980 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][C:26]1[CH:27]=[C:28]([CH:49]=[CH:50][CH:51]=1)[CH2:29][N:30]1[CH2:48][CH2:47][C:33]2([O:38][CH2:37][CH2:36][N:35]([C:39]([C:41]3[S:42][C:43]([CH3:46])=[CH:44][CH:45]=3)=[O:40])[CH2:34]2)[CH2:32][CH2:31]1.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:46][C:43]1[S:42][C:41]([C:39]([N:35]2[CH2:34][C:33]3([CH2:47][CH2:48][N:30]([CH2:29][C:28]4[CH:27]=[C:26]([CH2:25][CH:24]=[O:23])[CH:51]=[CH:50][CH:49]=4)[CH2:31][CH2:32]3)[O:38][CH2:37][CH2:36]2)=[O:40])=[CH:45][CH:44]=1

Participants

7

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 46240297(9-(3-(2-Hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

Product 1

HCID 579892992-(3-((4-(5-Methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)methyl)phenyl)acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (0.16 g) was added to a stirred solution of (9-(3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone (0.13 g) (example 9, step c) and trifluoroacetic acid (0.036 g) in DCM (4 mL) under nitrogen. After 0.5 h, saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL) were added and the reaction mixture extracted twice with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate and brine, dried over sodium sulphate, filtered and evaporated in vacuo to give the subtitled compound. Yield 0.13 g. Used directly.

Workup

  1. extractionthe reaction mixture extracted twice with ethyl acetate
  2. washThe combined organic extracts were washed with saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c0fc5836a681467694935096611343e6
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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