Hydrochloric Acid → HCID 86603417, compound

HRID 1028565Notes

Reaction equation

HRID 1028565 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:9](=[O:23])[C@@H:10]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1.CCC(C)[BH-](C(C)CC)C(C)CC.[Li+].Cl>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([C@H:9]([OH:23])[C@@H:10]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH3:11])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3611392Lithium tri-s-butylborohydrideHCID 67105363HCID 67105363, compound

Product 1

HCID 86603417HCID 86603417, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a −78° C. solution of benzyl [(1S)-2-(3,5-difluorophenyl)-1-methyl-2-oxoethyl]carbamate. (1.35 g, 4.23 mmol) in THF (75 mL) was added L-Selectride (6.35 mL of a 1M solution in THF, 6.35 mmol). After stirring at −78° C. for 1 hour, the reaction was poured into 1N HCl (50 mL). The mixture was extracted with EtOAc (2×100 mL). The organic extracts were washed with water and brine (50 mL each), dried over Na2SO4, filtered, and concentrated. Purification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes) afforded benzyl [(1S,2S)-2-(3,5-difluorophenyl)-2-hydroxy-1-methylethyl]carbamate (major product). LCMS=322.3 (M+1)+.

Workup

  1. customTo a −78° C.
  2. extractionThe mixture was extracted with EtOAc (2×100 mL)
  3. washThe organic extracts were washed with water and brine (50 mL each)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification of the residue by flash chromatography on silica gel (5 to 40% EtOAc/hexanes)

Sources & evidence

ORD record
ord-7eedcff7b9eb4132a52b52012b761091
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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