Tert-Butanesulfinamide → HCID 178455589, compound

HRID 245992Notes

Reaction equation

HRID 245992 reaction equation
[Si:1]([O:8][C@@H:9]1[CH2:12][C@H:11]([CH:13]=O)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:15][C:16]([S:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[Si:1]([O:8][C@@H:9]1[CH2:12][C@H:11](/[CH:13]=[N:21]/[S:19]([C:16]([CH3:18])([CH3:17])[CH3:15])=[O:20])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 178455373HCID 178455373, compound

Product 1

HCID 178455589HCID 178455589, compoundYield 48.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of cis-3-(tert-butyldimethylsilanyloxy)-cyclobutanecarbaldehyde (crude from step 3, 900 mg, 4.2 mmol) and 2-methylpropane-2-sulfinamide (509 mg, 4.2 mmol) in dry CH2Cl2 (10 mL) was added anhydrous CuSO4 (1.47 g, 9.24 mmol). The heterogeneous reaction mixture was stirred at room temperature overnight then filtered over Celite, rinsing with CH2Cl2. The filtrate was absorbed onto SiO2 and purified via chromatography with 0% to 20% EtOAc/hexanes to isolate 642 mg (48%) of 2-methyl-propane-2-sulfinic acid 1-[cis-3-(tert-butyldimethylsilanyloxy)-cyclobutyl]-meth-(E)-ylideneamide as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ (ppm) 8.04 (d, J=5.3 Hz, 1H), 4.25 (quin, J=7.4 Hz, 1H), 2.73-2.88 (m, 1H), 2.46-2.59 (m, 2H), 2.06-2.18 (m, 2H), 1.19 (s, 9H), 0.89 (s, 9H), 0.05 (s, 6H).

Workup

  1. filtrationthen filtered over Celite
  2. washrinsing with CH2Cl2
  3. customThe filtrate was absorbed onto SiO2
  4. custompurified via chromatography with 0% to 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-6f70dad1dc354a48ba98a4fd3662afcd
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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