Di-tert-butyl dicarbonate → HCID 68557056, compound

HRID 1869185Notes

Reaction equation

HRID 1869185 reaction equation
CNCCC(C1C=CC=CC=1)C1C2C(=NC=CC=2)NC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.[C:36]([O:40][C:41](=[O:62])[N:42]([CH3:61])[CH2:43][CH2:44][CH:45]([C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1)[C:46]1[C:54]2[C:49](=[N:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)([CH3:39])([CH3:38])[CH3:37]>C(Cl)Cl>[C:36]([O:40][C:41](=[O:62])[N:42]([CH3:61])[CH2:43][CH2:44][C@H:45]([C:55]1[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=1)[C:46]1[C:54]2[C:49](=[N:50][CH:51]=[CH:52][CH:53]=2)[NH:48][CH:47]=1)([CH3:39])([CH3:38])[CH3:37]

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 16725756N-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]amineHCID 68553855HCID 68553855, compound

Product 1

HCID 68557056HCID 68557056, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of racemic methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-amine (267 mg, 1.01 mmol) in DCM (40 ml) was added TEA (0.47 ml, 3.37 mmol) followed by Boc2O (416 mg, 1.91 mmol). The mixture was warmed to RT over 1 hour, and then stirred at RT for 22 hours to give a racemic mixture of Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-carbamic acid tert-butyl ester (not isolated). The reaction mixture was concentrated under reduced pressure, and purified via chiral preparative HPLC by multiple injections onto Chiralpak AD preparative 250×20 mm (hexane/i-PrOH, 6 ml/min), affording (R)-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-carbamic acid tert-butyl ester (215 mg, 31% yield) as a first fraction and (S)-Methyl-[3-phenyl-3-(1H-pyrrolo[2,3-b]pyridin-3-yl)-propyl]-carbamic acid tert-butyl estere (197 mg, 28% yield) as a second fraction.

Workup

  1. customto give
  2. customisolated)
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. custompurified via chiral preparative HPLC by multiple injections onto Chiralpak AD preparative 250×20 mm (hexane/i-PrOH, 6 ml/min)

Sources & evidence

ORD record
ord-13adc5129e0e43579468efebf4e1c721
Source dataset
uspto-grants-2009_12
Patent number
US07638517B2

Reaction notes

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