(2S,3R)-2-(N,N-Dibenzylamino)-3-tetradecanol → Xestoaminol C

HRID 722802Notes

Reaction equation

HRID 722802 reaction equation
C([N:8]([C@H:16]([C@H:18]([OH:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:17])CC1C=CC=CC=1)C1C=CC=CC=1>CO>[NH2:8][C@H:16]([C@H:18]([OH:30])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:17]

Participants

3

Reactant 1

HCID 58743372(2S,3R)-2-(N,N-Dibenzylamino)-3-tetradecanol

Product 1

HCID 14756407Xestoaminol CYield 86.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N,N-dibenzylamine 29 (182 mg, 0.44 mmol) in MeOH (4.5 mL) at room temperature, Pd(OH)2—C (20% wt, 24 mg, 0.04 mmol) was added. The mixture was purged with a stream of dry Ar, and then H2. The reaction was stirred overnight under a H2 atmosphere (1 atm). The catalyst was filtered off through a 0.45 μm teflon filter in polypropylene housing, washing the filter with MeOH (30 mL) and the solvent was evaporated in vacuo. The crude was purified by column chromatography on silica (90:10 CH2Cl2/MeOH to 100% MeOH) to obtain aminoalcohol 30 as a white solid (87 mg, 85% yield).

Workup

  1. customThe mixture was purged with a stream of dry Ar
  2. filtrationThe catalyst was filtered off through a 0.45 μm teflon
  3. filtrationfilter in polypropylene housing
  4. washwashing the
  5. filtrationfilter with MeOH (30 mL)
  6. customthe solvent was evaporated in vacuo
  7. customThe crude was purified by column chromatography on silica (90:10 CH2Cl2/MeOH to 100% MeOH)

Sources & evidence

ORD record
ord-b46565ab87d3423fbbe601489400bf0d
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

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