Acetic Acid → (2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-pyrrolidinemethanol

HRID 354425ノート

反応式

HRID 354425 の反応式
[C:1]([O:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:7]([CH2:17][O:18][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:6]1)(=[O:3])[CH3:2].C(O)(=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:1]([O:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C@H:7]([CH2:17][OH:18])[CH2:6]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 69340895(2S,4S)4-acetoxy-1-tert-butoxycarbonyl-2-tert-butyldiphenylsilyloxymethypyrrolidine

生成物 1

HCID 69332993(2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-pyrrolidinemethanol収率 79.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred mixture of (2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-tert-butyldiphenylsilyloxymethypyrrolidine (23.3 g, 46.9 mmol) and acetic acid (6.0 ml, 104.8 mmol) in THF (470 ml) was added TBAF (93.8 ml, 93.8 mmol) at 0° C. After 24 h stirring, the mixture was concentrated in vacuo. The resulting residue was diluted with EtOAC and aq. NH4Cl and extracted with EtOAc. The combined extracts were washed with brine, which were dried over Na2SO4 and concntrated in vacuo. The residue was chromatographed on silica gel (700 g, CHCl3/EtOAc (4/1)], to give (2S,4S)-4-acetoxy-1-tert-butoxycarbonyl-2-pyrrolidinemethanol (9.70 g, 8%) as a colorless oil. 1H-NMR (CDCl3) δ1.47 (s, 9H), 1.63 (m, 1H), 1.81 (m, 1H), 2.07 (s, 3H), 234 (m, 1H), 3.42 (dd, J=12.7, 0.9 Hz, 1H), 3.62-3.85 (m, 3H), 4.48 (br, 1H), 5.20 (br, 1H).

後処理

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe resulting residue was diluted with EtOAC and aq. NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined extracts were washed with brine, which
  5. dry with materialwere dried over Na2SO4
  6. customThe residue was chromatographed on silica gel (700 g, CHCl3/EtOAc (4/1)],

出典と根拠

ORDレコード
ord-f0c6640ccda3407f99f24e9b6f48e8c5
出典データセット
uspto-grants-2004_06
特許番号
US06756378B2

反応ノート

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