(2R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehyde → HCID 141625679, compound

HRID 2279520Notes

Reaction equation

HRID 2279520 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[O:8]1[C:12]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:11][CH2:10][C@@H:9]1[CH:18]=O>[O-]S([O-])(=O)=O.[Cu+2].C(Cl)Cl>[O:8]1[C:12]2([CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)[O:11][CH2:10][C@@H:9]1/[CH:18]=[N:7]\[S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6]

Participants

5

Reactant 2

HCID 10855919(2R)-1,4-Dioxaspiro[4.5]decane-2-carbaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 141625679HCID 141625679, compoundYield 49.1%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (S)-2-methylpropane-2-sulfinamide (4.7 g, 39 mmol) and DCM (15 mL) at RT was added anhydrous CuSO4 (14 g, 85 mmol) followed by a solution of (R)-1,4-dioxaspiro[4.5]decane-2-carbaldehyde (6.0 g, 35 mmol) and DCM (20 mL). The reaction was stirred at RT for 3 d then filtered through CELITE, washed with DCM and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with hexane/EtOAc (9:1 to 7:1) to afford 4.7 g (49%) of (S,Z)—N—((S)-1,4-dioxaspiro[4.5]decan-2-ylmethylene)-2-methylpropane-2-sulfinamide (248).

Workup

  1. filtrationthen filtered through CELITE
  2. washwashed with DCM
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by SiO2 chromatography
  5. washeluting with hexane/EtOAc (9:1 to 7:1)

Sources & evidence

ORD record
ord-526ef38d4fe8456194fdfff5adadc534
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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