Formaldehyde → HCID 53256022, compound

HRID 1844869Notes

Reaction equation

HRID 1844869 reaction equation
[NH:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])[CH2:2]1.[CH2:14]=O.[BH4-].[Na+].O>CO>[CH3:14][N:1]1[CH2:5][CH2:4][C@H:3]([NH:6][C:7](=[O:13])[O:8][C:9]([CH3:10])([CH3:12])[CH3:11])[CH2:2]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 4311764Sodium borohydride

Product 1

HCID 53256022HCID 53256022, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a dried reaction flask, (S)-tert-butyl pyrrolidin-3-ylcarbamate (5.774 g, 31.0 mmol) and formaldehyde solution (6.82 mL, 37%) were dissolved in methanol (124 mL) under a nitrogen atmosphere. The solution was stirred at room temperature for 1 hr. Sodium borohydride (3.518 g, 93.1 mmol) was added in portion under an ice bath. The solution was stirred at room temperature for 3 hr. Water was added to the reaction solution. After rotary-evaporation, ethyl acetate and saturated aqueous sodium bicarbonate solution were added. The reaction solution was extracted with ethyl acetate. The combined organic phase was washed with salt water, dried over anhydrous sodium sulfate, filtered, and purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:1) to produce a pale yellow solid (4.037 g) in 65% yield.

Workup

  1. stirringThe solution was stirred at room temperature for 3 hr
  2. customAfter rotary-evaporation, ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. additionwere added
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. washThe combined organic phase was washed with salt water
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. custompurified by silica gel column chromatography (ethyl acetate:petroleum ether=1:1)

Sources & evidence

ORD record
ord-0ed0e1f7ccbe44f49e879274e4d6e79a
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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