Methanol → HCID 68380511, compound

HRID 2175091Notes

Reaction equation

HRID 2175091 reaction equation
[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3[N:19]=[C:18]([N:20]4[CH2:25][CH2:24][CH:23]([NH:26][C:27]([C@@H:29]5[C@@H:33]([OH:34])[CH2:32][CH2:31][NH:30]5)=O)[CH2:22][CH2:21]4)[CH:17]=[CH:16][CH:15]=3)[CH:5]=[CH:4][C:3]1=2.CSC.B.B.CO>C1COCC1>[CH3:1][C:2]1([CH3:35])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3[N:19]=[C:18]([N:20]4[CH2:21][CH2:22][CH:23]([NH:26][CH2:27][C@@H:29]5[C@@H:33]([OH:34])[CH2:32][CH2:31][NH:30]5)[CH2:24][CH2:25]4)[CH:17]=[CH:16][CH:15]=3)[CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 6331BoraneHCID 12423031(Dimethyl sulfide)trihydroboron2×HCID 67248067HCID 67248067, compound

Product 1

HCID 68380511HCID 68380511, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

184 mg (0.39 mmol) of (2S,3S)-3-hydroxypyrrolidine-2-carboxylic acid [6′-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-3,4,5,6-tetrahydro-2H-1,2′-bipyridinyl-4-yl]amide was dissolved in 5 ml of THF, and 579 μl of 2M borane dimethyl sulfide solution in THF were added at 70° C. under nitrogen atmosphere, and the mixture was subsequently stirred at 70° C. for 2 hours. 579 μl of borane/dimethyl sulfide solution was again added, and the mixture was heated in a heating block at 70° C. for a further 4 hours. In order to decompose the excess borane, 1 ml of MeOH was added dropwise. The reaction mixture was evaporated, and 1 ml of water and 1 ml of conc HCl were added to the oily residue. The mixture was stirred at room temperature for 2 h, rendered alkaline using 2 molar NaOH and extracted with ethyl acetate. The organic phase was dried and purified by column chromatography on silica gel.

Workup

  1. temperaturethe mixture was heated in a heating block at 70° C. for a further 4 hours
  2. additionwas added dropwise
  3. customThe reaction mixture was evaporated
  4. addition1 ml of water and 1 ml of conc HCl were added to the oily residue
  5. stirringThe mixture was stirred at room temperature for 2 h
  6. extractionextracted with ethyl acetate
  7. customThe organic phase was dried
  8. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-d31e52187a244d08b6fbf18acd2f8a2c
Source dataset
uspto-grants-2015_06
Patent number
US09062015B2

Reaction notes

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