2-(Ethanesulfonyl)-1,3-benzothiazole → HCID 68710339, compound

HRID 2261901Notes

Reaction equation

HRID 2261901 reaction equation
[C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1[CH:10]=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH2:15](S(C1SC2C=CC=CC=2N=1)(=O)=O)[CH3:16].C[Si]([N-][Si](C)(C)C)(C)C.[Li+]>O1CCCC1>[C:4]([O:3][C:1]([N:8]1[CH2:14][CH2:13][CH2:12][C@@H:9]1/[CH:10]=[CH:15]/[CH3:16])=[O:2])([CH3:7])([CH3:6])[CH3:5]

Participants

5

Reactant 3

HCID 174282-(Ethanesulfonyl)-1,3-benzothiazoleHCID 2733832Lithium HexamethyldisilazideHCID 7009153N-(tert-Butoxycarbonyl)-D-prolinal

Product 1

HCID 68710339HCID 68710339, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a stirring solution of Boc-D-Prolinal (0.53 g, 2.65 mmol) and 2-(ethyl sulfonyl)-1,3-benzothiazole (1.5 g, 6.62 mmol) in tetrahydrofuran (4 mL) at −78° C. was added 1M Lithium bis(trimethylsilyl)amide in THF (4 mL) and continued stirring for 30 min. Then the mixture was warmed to 0° C. and stirred for an additional 3 hr. Upon completion via LC-MS, the reaction mixture was quenched with 20% ammonium chloride solution and extracted with ethyl ether. The ether layer washed with brine, dried over sodium sulfate anhydrous, filtered and dried in vacuo to yield crude product which was further purified on an ISCO normal phase HPLC using a 100% to 75% gradient of hexane to ethyl acetate as mobile phase. Pure tert-butyl-(2R)-2-[(1E)-prop-1-enyl]pyrrolidine-1-carboxylate was isolated from the combined fractions (0.09 g). 1H NMR (CD3OD, 400 Mhz) 5.51-5.44 ppm (m, 1H), 5.39-5.31 (m, 1H), 4.20-4.12 (m, 1H), 3.38-3.30 (m, 3H), 1.91-1.81 (m, 2H), 1.79-1.66 (m, 4H), 1.425 (s, 9H).

Workup

  1. stirringstirred for an additional 3 hr
  2. customUpon completion via LC-MS, the reaction mixture was quenched with 20% ammonium chloride solution
  3. extractionextracted with ethyl ether
  4. washThe ether layer washed with brine
  5. dry with materialdried over sodium sulfate anhydrous
  6. filtrationfiltered
  7. customdried in vacuo
  8. customto yield crude product which
  9. customwas further purified on an ISCO normal phase HPLC

Sources & evidence

ORD record
ord-4c3a89b674c54b2fa560a5376a4a68cb
Source dataset
uspto-grants-2010_12
Patent number
US07847100B2

Reaction notes

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