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

HRID 722823노트

반응식

HRID 722823 반응식
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]

참가 물질

4

반응물 1

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

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-83630ad523ed493bb455ccf9435fdefb
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138547B2

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