Aluminium lithium hydride → Carbamic acid, [(1R)-1-(hydroxymethyl)-3-butenyl]-, 1,1-dimethylethyl ester

HRID 1429379Notes

Reaction equation

HRID 1429379 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:14][CH:15]=[CH2:16])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH2:14][CH:15]=[CH2:16])[CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 58169888(R)-Methyl 2-((tert-butoxycarbonyl)amino)pent-4-enoate

Product 1

HCID 11106388Carbamic acid, [(1R)-1-(hydroxymethyl)-3-butenyl]-, 1,1-dimethylethyl esterYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of compound 18f (9.5 g, 41.5 mmol) in THF (50 mL) was cooled in an ice bath under argon. To this mixture was added LAH (3.9 g, 104 mmol) portionwise, and then the ice bath was removed and the reaction mixture was allowed to stir at rt for 2 h and then quenched with water (30 mL). The aqueous layer was extracted with EA (3×50 mL). The combined extracts were washed with brine, dried over Na2SO4, filtered, concentrated and purified by CC to give compound 18g (6.2 g, 75% yield) as yellow oil.

Workup

  1. customthe ice bath was removed
  2. customquenched with water (30 mL)
  3. extractionThe aqueous layer was extracted with EA (3×50 mL)
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC

Sources & evidence

ORD record
ord-a3d8afddfd48446ca424ceb43368a027
Source dataset
uspto-grants-2015_01
Patent number
US08940722B2

Reaction notes

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