tert-Butylsulfinamide, (R)-(+)- → HCID 87331639, compound

HRID 251737Notes

Reaction equation

HRID 251737 reaction equation
[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]=O)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].[C:15]([S@:19]([NH2:21])=[O:20])([CH3:18])([CH3:17])[CH3:16]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:1]([C:3]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]/[CH:13]=[N:21]/[S:19]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:20])[O:4][CH2:5][CH2:6][O:7]1)[CH3:2]

Participants

5

Reactant 2

HCID 10964479tert-Butylsulfinamide, (R)-(+)-HCID 86627961HCID 86627961, compound

Product 1

HCID 87331639HCID 87331639, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(2-ethyl-1,3-dioxolan-2-yl)hexanal (M3) (1.1 eq.), (R)-(+)-tert-butanesulfinamide (1.0 eq.) and anhydrous copper sulfate (2.2 eq.) in DCM was stirred for 70 h at RT. The reaction mixture was filtered through Celite. The solvent was removed under reduced pressure. The crude product was purified by flash chromatography with hexane/ethyl acetate mixture as eluent to yield the desired product as an oil. 1H NMR (300 MHz, CDCl3) δ: 8.05 (1H, t, J=4.6 Hz), 3.91 (4H, s), 2.60-2.40 (2H, m), 1.70-1.50 (6H, m), 1.47-1.28 (4H, m), 1.18 (9H, s), 0.88 (3H, t, J=7.5 Hz). 13C NMR (75 MHz, CDCl3) δ: 169.6, 111.9, 65.0, 56.5, 36.5, 36.0, 29.8, 29.5, 25.5, 23.5, 22.3, 8.1. MS (ES) C15H29NO3S requires: 303, found: 304 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customThe solvent was removed under reduced pressure
  3. customThe crude product was purified by flash chromatography with hexane/ethyl acetate mixture as eluent

Sources & evidence

ORD record
ord-d99af7be00c9466ca42bec8a8c4511ba
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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