Hydrochloric Acid → HCID 59438461, compound

HRID 2177531Notes

Reaction equation

HRID 2177531 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([N:23]=[N+]=[N-])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].Cl.[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][C:13]([NH2:23])([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 4311764Sodium borohydride2×HCID 59438450HCID 59438450, compound

Product 1

HCID 59438461HCID 59438461, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a refluxing solution of 500 mg (1.486 mmol) rac-3-azido-3-phenyl-piperidine-1-carboxylic acid benzyl ester (example A.1, step 2) and 281 mg (7.43 mmol) NaBH4 in THF (5 ml) was added dropwise 2.0 ml methanol over 1.5 hour. The mixture was refluxed for another hour and then stirred at room temperature overnight. Another 114 mg (3 mmol) NaBH4 were added and the mixture was refluxed for 2 hours. The mixture was cooled in an ice bath and acidified with HCl 1N. The mixture was basified with 1N NaOH and extracted three times with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 220 mg (48%) of the title compound as a colorless oil. MS (m/e): MS (m/e): 311.4 (M+H).

Workup

  1. customover 1.5 hour
  2. temperatureThe mixture was refluxed for another hour
  3. temperaturethe mixture was refluxed for 2 hours
  4. temperatureThe mixture was cooled in an ice bath
  5. extractionextracted three times with ethyl acetate
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

Sources & evidence

ORD record
ord-8c17a851c4c142cfb72741ebbe3e9ca4
Source dataset
uspto-grants-2015_06
Patent number
US09067911B2

Reaction notes

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