Cyclopentanecarbaldehyde → (NE,R)-N-(cyclopentylmethylidene)-2-methylpropane-2-sulfinamide

HRID 874738Notes

Reaction equation

HRID 874738 reaction equation
[CH:1]1([CH:6]=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:8]([S@:12]([NH-:14])=[O:13])([CH3:11])([CH3:10])[CH3:9]>[O-]S([O-])(=O)=O.[Cu+2]>[CH:1]1(/[CH:6]=[N:14]/[S@@:12]([C:8]([CH3:11])([CH3:10])[CH3:9])=[O:13])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 70106CyclopentanecarbaldehydeHCID 86609349(R)-t-butylsulfinylamide

Product 1

HCID 71812682(NE,R)-N-(cyclopentylmethylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

The title compound was synthesized according to General Method H utilizing cyclopentanecarboxaldehyde (15.0 g, 152.8 mmol, 1.0 eq.), (R)-t-butylsulfinylamide (24.1 g, 198.7 mmol, 1.3 eq.), and flame-dried CuSO4 (73.2 g, 458.5 mmol, 3.0 eq.). The resulting mixture was stirred at rt for 71 h. The reaction mixture was filtered through a pad of Celite and the pad was rinsed with CH2Cl2 (5×100 mL). The combined organic extracts were concentrated under reduced pressure yielding a clear yellow oil (37.2 g). Purification by flash chromatography (SiO2, h=6 cm, Ø=10 cm) using 1:9 EtOAc-cyclohexane as eluent gave the product (23.8 g, 78% isolated yield) as a clear pale yellow oil. 1H NMR (300 MHz, CDCl3) δ ppm 7.99 (d, J=5.5 Hz, 1H), 3.02-2.87 (m, 1H), 1.97-1.78 (m, 2H), 1.78-1.55 (m, 6H), 1.18 (s, 9H).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite
  2. washthe pad was rinsed with CH2Cl2 (5×100 mL)
  3. concentrationThe combined organic extracts were concentrated under reduced pressure

Sources & evidence

ORD record
ord-278a64e4a5d949e88fc54e7a346deffd
Source dataset
uspto-grants-2015_03
Patent number
US08980934B2

Reaction notes

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