Diisopropylethylamine → HCID 69543328, compound

HRID 2354056Notes

Reaction equation

HRID 2354056 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH2:12]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]1([C:21]2([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:25][CH2:24][NH:23][CH2:22]2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CCN(C(C)C)C(C)C>C1COCC1>[CH2:1]([O:8][C:9](=[O:14])[NH:10][CH2:11][CH2:12][N:23]1[CH2:24][CH2:25][C:21]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:22]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 278694benzyl N-(2-bromoethyl)carbamateHCID 4182423,3-Diphenylpyrrolidine

Product 1

HCID 69543328HCID 69543328, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(2-Bromo-ethyl)-carbamic acid benzyl ester (1.10 g, 4.26 mmol), 3,3-diphenyl-pyrrolidine (Example A18, 836 mg, 3.75 mmol) and DIPEA (1.0 mL 5.7 mmol) are dissolved in THF (20 mL) and stirred for 15 h at reflux. The mixture is quenched with Na2CO3 (50 mL) and extracted with CH2Cl2 (3×50 mL). The organic extracts are washed with sat. aq. Na2CO3 (30 mL), dried (Na2SO4), filtered and evaporated. The residue is purified by FC (SiO2, EtOAc-heptane) to provide the title compound.

Workup

  1. temperatureat reflux
  2. customThe mixture is quenched with Na2CO3 (50 mL)
  3. extractionextracted with CH2Cl2 (3×50 mL)
  4. washThe organic extracts are washed with sat. aq. Na2CO3 (30 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue is purified by FC (SiO2, EtOAc-heptane)

Sources & evidence

ORD record
ord-30a269241d094e2a82e9cc6723482ae1
Source dataset
uspto-grants-2010_07
Patent number
US07750161B2

Reaction notes

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