Lithium borohydride → HCID 57947907, compound

HRID 409867Notes

Reaction equation

HRID 409867 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:27])[C@H:9]([CH2:18][O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:10][C:11]([F:17])([F:16])[C:12](OC)=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>C1COCC1>[C:23]([O:22][C:20]([O:19][CH2:18][C@@H:9]([N:8]([CH3:27])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:10][C:11]([F:17])([F:16])[CH2:12][OH:13])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 57947619HCID 57947619, compound

Product 1

HCID 57947907HCID 57947907, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-methyl 4-(tert-butoxycarbonyl(methyl)amino)-5-(tert-butoxycarbonyloxy)-2,2-difluoropentanoate (42.0 g, 0.106 mol) in THF (300 mL) was added Lithium borohydride (79.3 mL, 2 M, 0.159 mol) in THF at 0° C. The reaction mixture was stirred at 0° C. for 1 h and at RT for 2 h. LC-MS showed the reaction was complete. The reaction mixture was concentrated and partitioned between EtOAc and H2O. After separating layers, the aqueous layer was extracted further with EtOAc. The combined organic layers were dried (Na2SO4), filtered, and concentrated, and the resulting residue was purified by silica gel column (hexanes/EtOAc) to give (S)-tert-butyl 1-(tert-butoxycarbonyloxy)-4,4-difluoro-5-hydroxypentan-2-yl(methyl)carbamate (35.3 g, 90%). LRMS (M+Na+) m/z 392.4.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between EtOAc and H2O
  3. customAfter separating layers
  4. extractionthe aqueous layer was extracted further with EtOAc
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe resulting residue was purified by silica gel column (hexanes/EtOAc)

Sources & evidence

ORD record
ord-5d7e28955338425d9c5657bb1debc138
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

Loading…