Tetrahydrofuran → 4-(4-But-2-ynyloxy-phenylsulfanylmethyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester

HRID 353552Notes

Reaction equation

HRID 353552 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12][CH2:13][C:14]2([C:27]([O:29]CC)=[O:28])[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[CH:8][CH:7]=1)[C:2]#[C:3][CH3:4].[OH-].[Na+].C1COCC1>CO>[C:23]([O:22][C:20]([N:17]1[CH2:18][CH2:19][C:14]([CH2:13][S:12][C:9]2[CH:10]=[CH:11][C:6]([O:5][CH2:1][C:2]#[C:3][CH3:4])=[CH:7][CH:8]=2)([C:27]([OH:29])=[O:28])[CH2:15][CH2:16]1)=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 697267481-(Tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy)phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate

Product 1

HCID 542579274-(4-But-2-ynyloxy-phenylsulfanylmethyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl esterYield 893.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.288 g (0.0643 mmol) of 1-(tert-butyl) 4-ethyl 4-({[4-(2-butynyloxy) phenyl]sulfanyl}methyl)-1,4-piperidinedicarboxylate, 3.25 mL of 1N NaOH 3.25 mL of THF and 3.25 mL of MeOH was heated to reflux for 3 h. The organics were removed and the residue was diluted with H2O, acidified and extracted with EtOAC. The organics were washed with H2O, brine, dried over mgSO4, filtered and concentrated in vacuo to provide 0.241 g (89%) of the desired product as an off white gum. Electrospray Mass Spec: 464.3 (M+FA−H)+.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe organics were removed
  4. additionthe residue was diluted with H2O
  5. extractionextracted with EtOAC
  6. washThe organics were washed with H2O, brine
  7. customdried over mgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5cab747bb19c4646b5d736881b7e6929
Source dataset
uspto-grants-2004_06
Patent number
US06753337B2

Reaction notes

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