tert-Butylsulfinamide, (R)-(+)- → HCID 178455588, compound

HRID 1404402Notes

Reaction equation

HRID 1404402 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]=O)[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19]([S@:23]([NH2:25])=[O:24])([CH3:22])([CH3:21])[CH3:20]>C1COCC1.[O-]CC.[Ti+4].[O-]CC.[O-]CC.[O-]CC>[CH2:1]([O:8][CH2:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14](/[CH:17]=[N:25]/[S@@:23]([C:19]([CH3:22])([CH3:21])[CH3:20])=[O:24])[CH2:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 178520941HCID 178520941, compound

Product 1

HCID 178455588HCID 178455588, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 76524Titanium tetraethoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (trans-4-(2-(benzyloxy)ethyl)cyclohexanecarbaldehyde (6.45 g, 26.18 mmol) and (R)-(+)-tert-butylsulfinamide (3.49 g, 28.8 mmol) in THF (66 mL) was added titanium(IV) ethoxide (8.78 mL, 41.89 mmol) under N2. The resulting solution was stirred at rt for 20 h and quenched by addition of saturated NaHCO3 solution dropwise. The mixture was vigorously stirred for 30 min and filtered through a pad of Celite, concentration. Purification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%) gave the titled product (8.38 g, 92%). LC/MC: 350.1 (MH)

Workup

  1. customquenched by addition of saturated NaHCO3 solution dropwise
  2. stirringThe mixture was vigorously stirred for 30 min
  3. filtrationfiltered through a pad of Celite, concentration
  4. customPurification by flash column chromatography (eluent: 20% EtOAc in hexanes to 30%)

Sources & evidence

ORD record
ord-e8747426db9145958fa622da58a8534a
Source dataset
uspto-grants-2014_12
Patent number
US08912169B2

Reaction notes

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