Water → (R)-3-Benzyloxy-2-(tert-butoxycarbonylamino)-propane

HRID 911245Notes

Reaction equation

HRID 911245 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH3:12])[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O>C1COCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:15]([O:11][CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH3:12])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 13200309tert-butyl N-((2R)-1-hydroxypropan-2-yl)carbamate

Product 1

HCID 11254115(R)-3-Benzyloxy-2-(tert-butoxycarbonylamino)-propaneYield 60.3%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Dissolve (R)-(+)-2-(tert-butoxycarbonylamino)-1-propanol (875 mg, 5 mmol) in anhydrous THF (50 mL). Add sodium hydride (60% in mineral oil, 210 mg, 5.2 mmol) and stir at 0° C. for 30 min. Add benzyl bromide (620 μL, 5.2 mmol) followed by tetrabutylammonium iodide (20 mg, 0.05 mmol) and stir for 3 h at ambient temperature. Pour the mixture into water (200 mL), extract with DCM (3×50 mL), wash with brine, dry over MgSO4, filter and concentrate. Purify by chromatography on silica gel eluting with hexane/EtOAc (19:1) to give the desired intermediate as a colorless oil (800 mg, 60%).

Workup

  1. extractionextract with DCM (3×50 mL)
  2. washwash with brine
  3. dry with materialdry over MgSO4
  4. filtrationfilter
  5. concentrationconcentrate
  6. customPurify by chromatography on silica gel eluting with hexane/EtOAc (19:1)

Sources & evidence

ORD record
ord-bdb2b583360049c5bdb93615bf40df7a
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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