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

HRID 722823ノート

反応式

HRID 722823 の反応式
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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-83630ad523ed493bb455ccf9435fdefb
出典データセット
uspto-grants-2006_11
特許番号
US07138547B2

反応ノート

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