tert-Butylsulfinamide, (S)-(-)- → HCID 140533337, compound

HRID 1367233Notes

Reaction equation

HRID 1367233 reaction equation
O=[CH:2][CH2:3][CH2:4][C@@:5]1([C:20]([O:22][CH3:23])=[O:21])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:24][C:25]([S@@:28]([NH2:30])=[O:29])([CH3:27])[CH3:26]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[C:25]([S@@:28](/[N:30]=[CH:2]/[CH2:3][CH2:4][C@@:5]1([C:20]([O:22][CH3:23])=[O:21])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:29])([CH3:27])([CH3:26])[CH3:24]

Participants

5

Reactant 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 86625742HCID 86625742, compound

Product 1

HCID 140533337HCID 140533337, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 1-benzyl 2-methyl (2R)-2-(3-oxopropyl)pyrrolidine-1,2-dicarboxylate from Step A (1.69 g, 5.29 mmol) and anhydrous CuSO4 (2.36 g, 10.6 mmol) in CH2Cl2 (10 mL) was added (S)-2-methylpropane-2-sulfinamide (0.641 g, 5.29 mmol). This mixture was stirred for 25 h before being filtered through a pad of celite. Additional CH2Cl2 was used to wash the celite. The combined organics were concentrated in vacuo to give a residue that was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—95:5 to 0:100, to give the title compound. MS: m/z=423 (M+1).

Workup

  1. filtrationbefore being filtered through a pad of celite
  2. washto wash the celite
  3. concentrationThe combined organics were concentrated in vacuo
  4. customto give a residue that
  5. customwas purified by silica gel chromatography
  6. washeluting with a gradient of hexane

Sources & evidence

ORD record
ord-65c850e924354b10959b0ccb78ea450c
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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