(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptane → HCID 69003591, compound

HRID 1984298Notes

Reaction equation

HRID 1984298 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10](Cl)=[O:11].[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]2[CH2:26][C@H:21]1[CH2:22][NH:23]2)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C(Cl)Cl.C([O-])(O)=O.[Na+]>[C:13]([O:17][C:18]([N:20]1[CH2:25][C@@H:24]2[CH2:26][C@H:21]1[CH2:22][N:23]2[C:10]([C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)=[O:11])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

5

Reactant 2

HCID 11521263(1S,4S)-2-Boc-2,5-diazabicyclo[2.2.1]heptaneHCID 118162081H-indole-2-carbonyl Chloride

Product 1

HCID 69003591HCID 69003591, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

To a 0° C. suspension of indole-2-carbonyl chloride (100 mg, 0.56 mmol) in CH2Cl2 was added a solution of TEA (235 μL, 1.67 mmol) and (S,S)-2,5-diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester (156 mg, 0.84 mmol) in CH2Cl2. After 1.5 h at 0° C., the mixture was diluted with saturated aqueous (satd. aq.) NaHCO3 and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with satd. aq. NaCl (20 mL), dried (Na2SO4), and concentrated to give a yellow liquid, which was purified by FCC to give a yellow solid (130 mg, 46%). 1H NMR (CDCl3): 9.37-9.17 (m, 1H), 7.70-7.64 (m, 1H), 7.47-7.41 (m, 1H), 7.35-7.28 (m, 1H), 7.19-7.10 (m, 1H), 6.86-6.78 (m, 1H), 5.13 (s, 1H), 4.77-4.50 (m, 1H), 4.02-3.80 (m, 1H), 3.80-3.39 (m, 2H), 2.08-1.88 (m, 2H), 1.54-1.35 (m, 9H).

Workup

  1. extractionextracted with CH2Cl2 (3×15 mL)
  2. washThe combined organic layers were washed with satd
  3. dry with materialaq. NaCl (20 mL), dried (Na2SO4)
  4. concentrationconcentrated
  5. customto give a yellow liquid, which
  6. customwas purified by FCC

Sources & evidence

ORD record
ord-bf0a92592e4748359ea1d03316b3a70a
Source dataset
uspto-grants-2009_06
Patent number
US07544698B2

Reaction notes

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