Carbon Tetrachloride → HCID 69419667, compound

HRID 1374979Notes

Reaction equation

HRID 1374979 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:20]([N:27]([C@@H:34]([CH3:37])[CH2:35]O)[CH2:28][C@H:29]([OH:33])[CH2:30][O:31][CH3:32])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl:38]C(Cl)(Cl)Cl>>[CH2:20]([N:27]([CH2:28][C@H:29]([OH:33])[CH2:30][O:31][CH3:32])[C@@H:34]([CH3:37])[CH2:35][Cl:38])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 57257357HCID 57257357, compound

Product 1

HCID 69419667HCID 69419667, compound

Procedure

Triphenylphosphine (10.09 g) was added to a solution of (2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-methoxypropyl]amino]-1-propanol (8.86 g) in tetrachloromethane (4.06 ml) at room temperature. After being stirred at room temperature for 2 days, the solution was concentrated under reduced pressure. The residue was triturated with diisopropyl ether (200 ml) three times, and the soluble portions were separated by decantation and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using mixed solvents of dichloromethane and methanol (40:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give (2S)-1-[N-benzyl-N-[(1S)-2-chloro-1-methylethyl]amino]-3-methoxy-2-propanol (4.90 g) as an oil.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. customThe residue was triturated with diisopropyl ether (200 ml) three times
  3. customthe soluble portions were separated by decantation
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel using
  6. additionmixed solvents of dichloromethane and methanol (40:1)
  7. additionThe fractions containing the objective compound
  8. customwere collected
  9. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-9e225d0fdc8f4435a7261dbd1cbe3952
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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