Tetrahydrofuran → Mmpsi

HRID 853841Notes

Reaction equation

HRID 853841 reaction equation
[O:1]=[C:2]1[C:10](=[O:11])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[CH:8]=2)[NH:3]1.C1COCC1.[CH3:21][O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][NH:25]1.C(N(CC)C(C)C)(C)C>C(Cl)(Cl)Cl>[CH3:21][O:22][CH2:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]1[S:12]([C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[NH:3][C:2](=[O:1])[C:10]2=[O:11])(=[O:14])=[O:13]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 671217(S)-(+)-2-(Methoxymethyl)pyrrolidineHCID 159089472,3-Dioxoindoline-5-sulfonyl chloride

Product 1

HCID 9840223MmpsiYield 93%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a cold suspension of 2,3-dioxo-2,3-dihydro-1H-indole-5-sulfonylchloride (5.28 g, 21.5 mmol) in a 1:1 mixture of THF:CHCl3 (254 mL) was added drop-wise via syringe pump a solution of (S)-(+)-2-(methoxymethyl)-pyrrolidine (3.45 mL, 28.0 mmol, 1.3 eq) (Aldrich) and N,N-diisopropylethylamine (7.49 mL, 43 mmol, 2 eq) in CHCl3 (42 mL) over a period of 70 minutes under a dry N2 atmosphere with cooling in an ice bath. After stirring an additional 20 minutes the mixture was concentrated. The residue was flash chromatographed (Biotage KP silica gel, 98/2 CH2Cl2/CH3OH) to give the title compound as a dark greenish-yellow foam (6.48 g. 93% yield). NMR (400 MHz, DMSO-d6): consistent MS: (API-ES−) m/z 323 [M−H].

Workup

  1. customof 70 minutes
  2. temperaturewith cooling in an ice bath
  3. concentrationwas concentrated
  4. customchromatographed (Biotage KP silica gel, 98/2 CH2Cl2/CH3OH)

Sources & evidence

ORD record
ord-6c1c4477004944fba369a02ac0d3a0f6
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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