(2S,3S)-2-(N-Benzyloxycarbonylamino)-3-octadecanol → (2S,3S)-2-Amino-3-octadecanol

HRID 722823Notes

Reaction equation

HRID 722823 reaction equation
C(OC([NH:11][C@H:12]([C@@H:14]([OH:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:13])=O)C1C=CC=CC=1>CO.[Pd]>[NH2:11][C@H:12]([C@@H:14]([OH:30])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:13]

Participants

4

Reactant 1

HCID 58743388(2S,3S)-2-(N-Benzyloxycarbonylamino)-3-octadecanol

Product 1

HCID 57017700(2S,3S)-2-Amino-3-octadecanolYield 89%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-benzyloxycarbonylamine 90 (330 mg, 0.79 mmol) in MeOH (40 mL) at room temperature, Pd—C (10% wt, 100 mg, 0.09 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 (50 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 91 as a white solid (200 mg, 89% 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 (50 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-83630ad523ed493bb455ccf9435fdefb
Source dataset
uspto-grants-2006_11
Patent number
US07138547B2

Reaction notes

Loading…