Methanol → HCID 57327211, compound

HRID 1850150Notes

Reaction equation

HRID 1850150 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH:14]1[CH2:16][CH2:15]1)[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[BH4-].CO>CCOCC>[CH:14]1([C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[CH2:10][OH:11])[CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 887MethanolHCID 4148881Lithium borohydrideHCID 75487983HCID 75487983, compound

Product 1

HCID 57327211HCID 57327211, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of (S)-methyl 2-(tert-butoxycarbonylamino)-2-cyclopropylacetate (5.35 g, 23.33 mmol) in Et2O (100 ml) was added LiBH4 (0.762 g, 35.0 mmol), followed by drop wise addition of methanol (1.420 ml, 35.0 mmol). The reaction was refluxed at 40° C. for one hour. The reaction mixture was then cooled to 0° C., and quenched with HCl (1M) until pH=2 for aqueous layer. The phases were separated and the aqueous layer was extracted with DCM (3×100 mL). The organic was then dried (Na2SO4) and concentrated under reduced pressure to give final crude product (4.16 g). LCMS m/z 224.1 (M+Na)+, Rt 0.62 min.

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customquenched with HCl (1M) until pH=2 for aqueous layer
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with DCM (3×100 mL)
  5. dry with materialThe organic was then dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f18212d9d70740518c53b554bdea9ca2
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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