Sodium Hydroxide → HCID 67126440, compound

HRID 2040190Notes

Reaction equation

HRID 2040190 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.C(O[C:17]1(O[Si](C)(C)C)[CH2:19][CH2:18]1)C.C([BH3-])#N.[Na+].[OH-].[Na+]>CO.C(O)(=O)C>[CH:17]1([N:1]2[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]2)[CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 1514396(3S)-(-)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydride

Product 1

HCID 67126440HCID 67126440, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

(S)-tert-butyl pyrrolidin-3-ylcarbamate (415 mg), (1-ethoxycyclopropoxy)trimethylsilane (1.8 mL) and molecular sieves (500 mg) were combined in methanol (4.5 mL). Acetic acid (1.3 mL) was added, followed by sodium cyanoborohydride (420 mg). The resulting mixture was heated to reflux for 4 hours. Insoluble material was filtered off and reaction was made basic to pH 14 with addition of 6M aqueous NaOH solution. The solution was extracted three times with diethyl ether, and the combined extracts were dried over MgSO4, filtered and concentrated to obtain an oil, which was purified by flash chromatography, eluting first with 100% dichloromethane, followed by 5% methanol/dichloromethane and 10% methanol/dichloromethane.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 hours
  3. filtrationInsoluble material was filtered off
  4. customreaction
  5. extractionThe solution was extracted three times with diethyl ether
  6. dry with materialthe combined extracts were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto obtain an oil, which
  10. customwas purified by flash chromatography
  11. washeluting first with 100% dichloromethane

Sources & evidence

ORD record
ord-5a38e2191f274bb28c32cc3f8bba9bbb
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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