Sodium Bicarbonate → tert-Butyl [(2R)-1-hydroxypent-4-yn-2-yl]carbamate

HRID 522233Notes

Reaction equation

HRID 522233 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH3:7][C:8]([O:11][C:12]([NH:14][C@@H:15]([C:19]([O-])=[O:20])[CH2:16][C:17]#[CH:18])=[O:13])([CH3:10])[CH3:9].C([O-])(O)=O.[Na+]>O1CCCC1.O>[C:8]([O:11][C:12](=[O:13])[NH:14][C@H:15]([CH2:16][C:17]#[CH:18])[CH2:19][OH:20])([CH3:10])([CH3:9])[CH3:7]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 7009125HCID 7009125, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 27281774tert-Butyl [(2R)-1-hydroxypent-4-yn-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

An oven-dried, nitrogen-flushed 3-neck 500 mL round bottom flask equipped with a pressure-equalizing addition funnel was charged with LiAlH4 (1N in tetrahydrofuran, 46.9 ml, 46.9 mmol), and the flask was chilled in an ice-water bath. A solution of (R)—N-Boc-propargylglycine (5.0 g, 23.45 mmol) in tetrahydrofuran (100 ml) was then added dropwise through the funnel, controlling the addition so that the bubbling was not too vigorous. The reaction was allowed to come to room temperature and was stirred overnight, and chilled in an ice bath. Saturated aqueous NaHCO3 solution (15 mL) was added dropwise over about 0.5 hours. The resulting suspension was diluted with water (˜25 mL) and filtered through diatomaceous earth, rinsing with ether. The filtrate was transferred to a separatory funnel and the layers were separated. The organic phase was washed with saturated Rochelle's salt, water and brine then dried (Na2SO4), filtered and concentrated to give the title compound, which was used without further purification.

Workup

  1. customAn oven-dried, nitrogen-flushed 3-neck 500 mL round bottom flask
  2. customequipped with a pressure-equalizing addition funnel
  3. temperaturethe flask was chilled in an ice-water bath
  4. additionthe addition so that the bubbling
  5. customto come to room temperature
  6. temperaturechilled in an ice bath
  7. filtrationfiltered through diatomaceous earth
  8. washrinsing with ether
  9. customThe filtrate was transferred to a separatory funnel
  10. customthe layers were separated
  11. washThe organic phase was washed with saturated Rochelle's salt, water and brine
  12. dry with materialthen dried (Na2SO4)
  13. filtrationfiltered
  14. concentrationconcentrated

Sources & evidence

ORD record
ord-8f6b59fbe2594ba289811dcb64139ab8
Source dataset
uspto-grants-2016_05
Patent number
US09328112B2

Reaction notes

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