Ethyl chloroformate → HCID 69585940, compound

HRID 1242073Notes

Reaction equation

HRID 1242073 reaction equation
Cl.[O:2]1[C:6]2([CH2:11][CH2:10][NH:9][CH:8]([CH2:12][N:13]3[C:21](=[O:22])[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]3=[O:23])[CH2:7]2)[O:5][CH2:4][CH2:3]1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH2:28]([O:27][C:25]([N:9]1[CH2:10][CH2:11][C:6]2([O:5][CH2:4][CH2:3][O:2]2)[CH2:7][CH:8]1[CH2:12][N:13]1[C:14](=[O:23])[C:15]2[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:21]1=[O:22])=[O:26])[CH3:29]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 21936741HCID 21936741, compound

Product 1

HCID 69585940HCID 69585940, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of the above 2-(1,4-dioxa-8-aza-spiro[4.5]dec-7-ylmethyl)-isoindole-1,3-dione hydrochloride (0.7 g, 2.1 mmol) and ethyl chloroformate (0.24 ml, 2.5 mmol) in dry tetrahydrofuran (14 ml) cooled in an ice bath under nitrogen was added diisopropylethylamine (0.95 ml, 5.4 mmol) and the reaction mixture was stirred at ambient temperature for 3 hours. The volatiles were removed in vacuo and the residue was partitioned between dichloromethane (25 ml) and 1N hydrochloric acid (25 ml). The layers were separated, and the aqueous layer extracted with dichloromethane (20 ml). The combined organic extracts were washed with a saturated sodium bicarbonate solution (50 ml), dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was triturated with n-butylchloride, filtered and dried with nitrogen which afforded 0.47 g (61%) of 7-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-1,4-dioxa-8-aza-spiro[4.5]decane-8-carboxylic acid ethyl ester.

Workup

  1. temperaturecooled in an ice bath under nitrogen
  2. customThe volatiles were removed in vacuo
  3. customthe residue was partitioned between dichloromethane (25 ml) and 1N hydrochloric acid (25 ml)
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted with dichloromethane (20 ml)
  6. washThe combined organic extracts were washed with a saturated sodium bicarbonate solution (50 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent evaporated in vacuo
  10. customThe residue was triturated with n-butylchloride
  11. filtrationfiltered
  12. customdried with nitrogen which

Sources & evidence

ORD record
ord-75d77856c5284fedbda7ee5bcd310080
Source dataset
uspto-grants-2006_10
Patent number
US07115624B1

Reaction notes

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