Diethyl Pyrocarbonate → HCID 178495709, compound

HRID 735773Notes

Reaction equation

HRID 735773 reaction equation
Cl.[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH2:26])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1.C(N(CC)CC)C.[NH:34]1[C:38]2[CH:39]=[CH:40][C:41]([C:43](O)=[O:44])=[CH:42][C:37]=2[N:36]=[N:35]1.CCOC(OC(OCC)=O)=O>C1COCC1.O>[CH3:2][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH:26][C:43]([C:41]3[CH:40]=[CH:39][C:38]4[NH:34][N:35]=[N:36][C:37]=4[CH:42]=3)=[O:44])=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1

Participants

7

Reactant 4

HCID 3051Diethyl PyrocarbonateHCID 8471TriethylamineHCID 67150575(1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochlorideHCID 178524184HCID 178524184, compound

Product 1

HCID 178495709HCID 178495709, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution (5 ml) of (1R,2S)-2-{[(3aR,4R,9bR)-4-(methoxymethyl)-2,3,3a,4,5,9b-hexahydro-1H-pyrrolo[3,2-c]quinolin-1-yl]carbonyl}cyclohexaneamine hydrochloride (200 mg, 0.480 mmol) in THF were added triethylamine (0.199 ml, 1.44 mmol), 1H-1,2,3-benzotriazole-5-carboxylic acid (78.3 mg, 0.480 mmol) and DEPC (0.079 ml, 0.528 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained residue was subjected to column chromatography using silica gel and eluted with hexane:ethyl acetate (1:1-1:9) to give the title compound (187 mg, 80%) as an amorphous form.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. washeluted with hexane:ethyl acetate (1:1-1:9)

Sources & evidence

ORD record
ord-60afdb3cd5af492f8ba92324e0623853
Source dataset
uspto-grants-2009_09
Patent number
US07592453B2

Reaction notes

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