Trimethyl orthoformate → HCID 9827593, compound

HRID 351167Notes

Reaction equation

HRID 351167 reaction equation
C(OC([N:8]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([CH2:16][NH:17][CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:12][CH:11]=1)=O)(C)(C)C.C([N:42]1[CH2:46][CH2:45][C:44](=O)[CH2:43]1)(OC(C)(C)C)=O.COC(OC)OC.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[CH2:28][NH:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]([CH:44]2[CH2:45][CH2:46][NH:42][CH2:43]2)[CH:18]2[C:27]3[N:26]=[CH:25][CH:24]=[CH:23][C:22]=3[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 471360Tert-butyl 3-oxopyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 22018600N-(t-butoxycarbonyl)-N-(2-pyridinylmethyl)-N'-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine

Product 1

HCID 9827593HCID 9827593, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

To the solution of N-(t-butyloxycarbonyl)-N-(2-pyridinylmethyl)-N′-(5,6,7,8-tetrahydro-8-quinolinyl)-1,4-benzenedimethanamine (195 mg, 0.43 mmol) and N-Boc-3-pyrrolidone (91 mg, 0.49 mmol) in methanol (3 ml) was added trimethylorthoformate (2 ml) and three drops of acetic acid, at room temperature. This mixture was allowed to stir for 30 min. at room temperature and sodium cyanoborohydride (130 mg, 2.09 mmol) was added. Stirring was continued for a further 18 hours at room temperature and then the reaction mixture was concentrated. The residue was dissolved in ethylacetate (300 mL), and washed with saturated aqueous NaHCO3 and brine, then dried (Na2SO4) and evaporated. Purification of the residue by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2) gave the desired product (120 mg, 45%) as a mixture of diastereomers.

Workup

  1. customat room temperature
  2. stirringStirring
  3. waitwas continued for a further 18 hours at room temperature
  4. concentrationthe reaction mixture was concentrated
  5. dissolutionThe residue was dissolved in ethylacetate (300 mL)
  6. washwashed with saturated aqueous NaHCO3 and brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated
  9. customPurification of the residue by column chromatography on silica gel (1.5×20 cm, 50:50 EtOAc/CH2Cl2)

Sources & evidence

ORD record
ord-3fcb0949974c4e2c923c159c3f6d7f0e
Source dataset
uspto-grants-2007_02
Patent number
US07183273B2

Reaction notes

Loading…