Triethylamine → HCID 59653661, compound

HRID 2052758Notes

Reaction equation

HRID 2052758 reaction equation
[OH:1][N:2]1[C:11](=[O:12])[CH:10]2[CH:5]([CH:6]3[CH2:13][CH:9]2[CH:8]=[CH:7]3)[C:3]1=[O:4].Cl[CH2:15][CH2:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C.[CH:28]1([SH:34])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1.O>[CH:28]1([S:34][CH2:15][CH2:16][S:17]([O:1][N:2]2[C:11](=[O:12])[CH:10]3[CH:5]([CH:6]4[CH2:13][CH:9]3[CH:8]=[CH:7]4)[C:3]2=[O:4])(=[O:19])=[O:18])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 15290CyclohexanethiolHCID 15385Ethanesulfonylchloride, 2-chloro-HCID 895293a,4,7,7a-Tetrahydro-2-hydroxy-4,7-methano-1H-isoindole-1,3(2H)-dione

Product 1

HCID 59653661HCID 59653661, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5.38 g (30.0 mmol) of N-hydroxy-5-norbornene-2,3-dicarboximide in THF (75 ml) is treated successively with 2-chloroethanesulfonyl chloride (3.47 ml, 33.0 mmol) and triethylamine (9.6 ml, 69.0 mmol) while cooling over an ice-bath. After stirring for 1 h at 0° C. triethylamine (6.3 ml, 45.0 mmol) is added first, followed by the addition of cyclohexanethiol (4.05 ml, 33.0 mmol). The beige suspension is further stirred for 1 h at room temperature, then poured into water (140 ml) and extracted two times with ethyl acetate (300 ml). The combined organic phases are washed with water (300 ml), dried over MgSO4, and concentrated. The residue is purified by flash chromatography on silica gel with hexane and ethyl acetate (7:3) as eluent, yielding 9.22 g of the product as a white solid. The, structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 1.21-1.40 (m, 6H), 1.50-1.56 (m, 1H), 1.58-1.67 (m, 1H), 1.74-1.85 (m, 3H), 1.92-2.04 (m, 2H), 2.67-2.79 (m, 1H), 3.03-3.11 (m, 2H), 3.34 (s, 2H), 3.48 (s, 2H), 3.62-3.70 (m, 2H), 6.19 (s, 2H). mp. 96-98° C.

Workup

  1. temperaturewhile cooling over an ice-bath
  2. additionis added first
  3. extractionextracted two times with ethyl acetate (300 ml)
  4. washThe combined organic phases are washed with water (300 ml)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. customThe residue is purified by flash chromatography on silica gel with hexane and ethyl acetate (7:3) as eluent

Sources & evidence

ORD record
ord-0b0f34cdaeb74cb6aa80d8fd1fcd266d
Source dataset
uspto-grants-2008_02
Patent number
US07326511B2

Reaction notes

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