Lithium borohydride → HCID 86710445, compound

HRID 1398474Notes

Reaction equation

HRID 1398474 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][CH:15]=[C:16]([F:18])[F:17])[C:10](OC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+]>O1CCCC1>[F:17][C:16]([F:18])=[CH:15][CH2:14][C@H:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:10][OH:11]

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 86710444HCID 86710444, compound

Product 1

HCID 86710445HCID 86710445, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

An ambient temperature solution of (S)-methyl 2-((tert-butoxycarbonyl)amino)-5,5-difluoropent-4-enoate (1.91 g, 7.20 mmol) in tetrahydrofuran (25 mL) was treated with lithium borohydride (0.31 g, 14 mmol) and stirred for 1 h. The resulting solution was cooled to 5° C., quenched with 0.1 N aqueous hydrochloric acid (50 mL), and extracted with ethyl acetate (3×25 mL). The pooled organic extracts were washed with brine (1×20 mL), dried over MgSO4, and concentrated under reduced pressure. The crude material was purified over SiO2 (20-100% ethyl acetate/hexanes gradient elution) to afford (S)-tert-butyl (5,5-difluoro-1-hydroxypent-4-en-2-yl)carbamate (1.4 g, 5.90 mmol, 82% yield) as a colorless oil. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 4.75 (d, J=6.0 Hz, 1H), 4.35-4.05 (m, 1H), 3.82-3.51 (m, 3H), 2.46-2.16 (m, 3H), 1.47 (s, 9H).

Workup

  1. customquenched with 0.1 N aqueous hydrochloric acid (50 mL)
  2. extractionextracted with ethyl acetate (3×25 mL)
  3. washThe pooled organic extracts were washed with brine (1×20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe crude material was purified over SiO2 (20-100% ethyl acetate/hexanes gradient elution)

Sources & evidence

ORD record
ord-9a8e089ffc3b457d9b628366db437cd3
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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