Potassium borohydride → HCID 11242828, compound

HRID 1660701Notes

Reaction equation

HRID 1660701 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5](=[O:18])[C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH3:9])[CH3:8].[BH4-].[K+]>CO>[CH3:1][O:2][C:3](=[O:19])[CH2:4][C@H:5]([OH:18])[C@H:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:7]([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 4192641Potassium borohydrideHCID 11231121HCID 11231121, compound

Product 1

HCID 11242828HCID 11242828, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of methyl ester 45 (2.4 g, 8.70 mmol) in HPLC MeOH (100 mL), cooled to −78° C., potassium borohydride (1.4 g, 26.1 mmol) was added in portions. The reaction mixture was stirred at −78° C. for 10 min, warmed to −20° C. for 30 min and then to 0° C. for 10 min. The reaction was quenched with acetic acid to pH=7 and extracted with CH2Cl2 (3×50 mL). The organic layer was washed with NaHCO3 (50 mL, sat), NaCl (50 mL, sat), dried (Na2SO4), filtered, and evaporated. The alcohol 46 was obtained as a colorless oil (2.2 g, 92%) and used directly in the next step. 1H-NMR (500 MHz, CDCl3): 0.88 (d, J=6.8 Hz, 3H), 0.93 (d, J=6.8 Hz, 3H), 1.44 (s, 9H), 2.03-2.17 (m, 1H), 2.41-2.52 (m, 1H), 2.58-2.63 (m, 1H), 3.50-3.55 (m, 1H), 3.71 (s, 3H), 3.89-3.93 (m, 1H), 3.38-3.41 (m, 1H).

Workup

  1. temperaturewarmed to −20° C. for 30 min
  2. waitto 0° C. for 10 min
  3. customThe reaction was quenched with acetic acid to pH=7
  4. extractionextracted with CH2Cl2 (3×50 mL)
  5. washThe organic layer was washed with NaHCO3 (50 mL, sat), NaCl (50 mL, sat)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-b527e6c09a0b4d30ac47c25a6b1b6954
Source dataset
uspto-grants-2011_10
Patent number
US08030279B2

Reaction notes

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