Trifluoroacetic acid → 2-(3-((4-(Benzo[b]thiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)-2-fluorophenyl)acetaldehyde

HRID 1689411Notes

Reaction equation

HRID 1689411 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[S:23]1[C:27]([C:28]([N:30]2[CH2:35][C:34]3([CH2:40][CH2:39][N:38]([CH2:41][C:42]4[CH:47]=[CH:46][CH:45]=[C:44]([CH2:48][CH2:49][OH:50])[C:43]=4[F:51])[CH2:37][CH2:36]3)[O:33][CH2:32][CH2:31]2)=[O:29])=[CH:26][C:25]2[CH:52]=[CH:53][CH:54]=[CH:55][C:24]1=2.FC(F)(F)C(O)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[S:23]1[C:27]([C:28]([N:30]2[CH2:35][C:34]3([CH2:40][CH2:39][N:38]([CH2:41][C:42]4[C:43]([F:51])=[C:44]([CH2:48][CH:49]=[O:50])[CH:45]=[CH:46][CH:47]=4)[CH2:37][CH2:36]3)[O:33][CH2:32][CH2:31]2)=[O:29])=[CH:26][C:25]2[CH:52]=[CH:53][CH:54]=[CH:55][C:24]1=2

Participants

8

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 57989186Benzo[b]thiophen-2-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Product 1

HCID 579893902-(3-((4-(Benzo[b]thiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)-2-fluorophenyl)acetaldehyde

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dess-Martin periodinane (0.282 g) was added to a stirred solution of benzo[b]thiophen-2-yl(9-(2-fluoro-3-(2-hydroxyethyl)benzyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone (example 79, step b) (0.240 g) and trifluoroacetic acid (0.059 mL) in DCM (5 mL). After 1 h, ethyl acetate (30 mL) was added followed by a mixture of saturated sodium thiosulphate solution (5 mL) and saturated sodium bicarbonate solution (5 mL). The reaction mixture was shaken well and separated. The ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine. Acetic acid (0.08 mL) was added, then the solution was dried over sodium sulphate, filtered and evaporated in vacuo (bath temperature ˜30° C.) to give the subtitled compound as a gum. Yield 0.24 g. Used directly.

Workup

  1. customseparated
  2. washThe ethyl acetate solution was washed with saturated sodium bicarbonate solution, water and brine
  3. additionAcetic acid (0.08 mL) was added
  4. dry with materialthe solution was dried over sodium sulphate
  5. filtrationfiltered
  6. customevaporated in vacuo (bath temperature ˜30° C.)

Sources & evidence

ORD record
ord-7ccb6d226eff40fcabbbbc5ab29bdf9f
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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