HCID 69678038、化合物 → HCID 69677833、化合物

HRID 1072064ノート

反応式

HRID 1072064 の反応式
[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH:16]=[CH:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CCOC(C)=O.[Pd]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][CH2:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[OH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[CH:11][C:10]=1[CH2:16][CH2:17][C@H:18]([OH:29])[C@@H:19]([O:21][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:23])[CH3:24])[CH3:20]

参加物

5

反応物 1

HCID 69678038HCID 69678038、化合物

生成物 2

HCID 69677833HCID 69677833、化合物収率 51.3%HCID 69678558HCID 69678558、化合物収率 45.5%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-1-penten-3-ol (2.62 g) and 10% Pd—C (0.52 g) in EtOAc (65 ml) was stirred under hydrogen atmosphere at atmospheric pressure for 13 min. Pd—C was removed by filtration and the filtrate was evaporated. The residual oil (2.38 g) was chromatographed over silica gel (30 g) eluting with a mixture of hexane and EtOAc (50:1 to 2:1) to give a colorless oil of (3S,4S)-1-(2-benzyloxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-3-pentanol (1.35 g, 51.3%) and (3S,4S)-1-(2-hydroxy-4-fluorophenyl)-4-tert-butyldimethylsilyloxy-3-pentanol (0.94 g, 45.5%).

後処理

  1. customPd—C was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe residual oil (2.38 g) was chromatographed over silica gel (30 g)
  4. washeluting with a mixture of hexane and EtOAc (50:1 to 2:1)

出典と根拠

ORDレコード
ord-70bb84863613424994efe1a9f801e6e9
出典データセット
uspto-grants-2005_06
特許番号
US06908940B2

反応ノート

読み込み中…