Hydrochloric Acid → HCID 68019346, compound

HRID 456250Notes

Reaction equation

HRID 456250 reaction equation
[N:1]([C@@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@H:5]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[N+]=[N-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.Cl>C1(C)C=CC=CC=1.C1COCC1>[NH2:1][C@@H:4]1[CH2:8][N:7]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@H:5]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:21])([CH3:20])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11776TriphenylphosphineHCID 86666332HCID 86666332, compound

Product 1

HCID 68019346HCID 68019346, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl (3R,4R)-4-azido-1-benzylpyrrolidin-3-ylcarbamate (7.0 g, 22.0 mmol) in 250 mL toluene, PPh3 6.0 g, 23.0 mmol) was added and the mixture was refluxed for 1 hour. The mixture was cooled down to room temperature, diluted with 250 mL THF, water (0.54 g, 30.0 mmol) was added and the mixture was refluxed for an additional 1 hour. 4N HCl was added, the aqueous acidic layer was separated, washed with CHCl3 and basified with aqueous NH3 to pH 9-10. The product was extracted with CHCl3, the combined organic extracts were dried with Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel eluting with 10% MeOH in CHCl3 giving the title mono-Boc protected diamine.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. additionwas added
  3. temperaturethe mixture was refluxed for an additional 1 hour
  4. customthe aqueous acidic layer was separated
  5. washwashed with CHCl3 and basified with aqueous NH3 to pH 9-10
  6. extractionThe product was extracted with CHCl3
  7. dry with materialthe combined organic extracts were dried with Na2SO4
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel eluting with 10% MeOH in CHCl3 giving the title mono-Boc

Sources & evidence

ORD record
ord-93ef61a253ff4df5acee790372cefd11
Source dataset
uspto-grants-2013_07
Patent number
US08497383B2

Reaction notes

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