Formic Acid → 3-(2-(4-(5-Methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)-ethyl)benzaldehyde

HRID 471013Notes

Reaction equation

HRID 471013 reaction equation
C(O)=O.C([O:6][CH:7](OCC)[C:8]1[CH:9]=[C:10]([CH:32]=[CH:33][CH:34]=1)[CH2:11][CH2:12][N:13]1[CH2:31][CH2:30][C:16]2([O:21][CH2:20][CH2:19][N:18]([C:22]([C:24]3[S:25][C:26]([CH3:29])=[CH:27][CH:28]=3)=[O:23])[CH2:17]2)[CH2:15][CH2:14]1)C>O1CCCC1.O>[CH3:29][C:26]1[S:25][C:24]([C:22]([N:18]2[CH2:17][C:16]3([CH2:30][CH2:31][N:13]([CH2:12][CH2:11][C:10]4[CH:9]=[C:8]([CH:34]=[CH:33][CH:32]=4)[CH:7]=[O:6])[CH2:14][CH2:15]3)[O:21][CH2:20][CH2:19]2)=[O:23])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 57988993(9-(3-(Diethoxymethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone

Product 1

HCID 579893523-(2-(4-(5-Methylthiophene-2-carbonyl)-1-oxa-4,9-diazaspiro[5,5]undecan-9-yl)-ethyl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Formic acid (2 mL) was added to stirred solution of (9-(3-(diethoxymethyl)phenethyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(5-methylthiophen-2-yl)methanone (example 20, step e) (0.20 g) in tetrahydrofuran (3 mL) and water (1 mL) cooled in an ice bath. After 10 min, the reaction mixture was evaporated in vacuo, toluene was added and the reaction mixture was evaporated in vacuo. The residue was dissolved in acetonitrile and then evaporated in vacuo, and this process was repeated to give the subtitled compound as an oil that was used directly. Yield 0.16 g.

Workup

  1. temperaturecooled in an ice bath
  2. customthe reaction mixture was evaporated in vacuo, toluene
  3. additionwas added
  4. customthe reaction mixture was evaporated in vacuo
  5. dissolutionThe residue was dissolved in acetonitrile
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-ca4f46956952480d84262dc08730c565
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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