Dimethyl Sulfide → (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol

HRID 354415ノート

反応式

HRID 354415 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[C:24](O)=[O:25])=[O:7])([CH3:4])([CH3:3])[CH3:2].CSC>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH2:10][C@H:9]1[CH2:24][OH:25])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

4

反応物 2

HCID 1068Dimethyl SulfideHCID 2756011(2S,4S)-1-(Tert-butoxycarbonyl)-4-(2-naphthyloxy)-2-pyrrolidinecarboxylic acid

生成物 1

HCID 67405321(2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol収率 102.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylcarboxylic acid (1.12 g, 3.13 mmol) in THF (30 ml) was added BH3.DMS (0.63 ml, 6.3 mmol) at 0° C. The mixture was raised to room temperature immediately and then heated at 50° C. for 1.5 h. After cooling to room temperature, the mixture was quenched by the addition of water at 0° C. and extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and evaporated. The residue was chromatographed on silica gel [50 g, CHCl3/MeOH (50/1)], to give (2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethanol (1.10 g, 100%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.48 (s, 9H), 2.45 (m, 1H), 3.58-4.80 (m, 4H), 5.01 (br, 1H), 7.04-7.99 (m, 7H).

後処理

  1. customat 0° C
  2. temperatureheated at 50° C. for 1.5 h
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was quenched by the addition of water at 0° C.
  5. extractionextracted with EtOAc
  6. washThe combined extracts were washed with brine
  7. dry with materialdried over Na2SO4
  8. customevaporated
  9. customThe residue was chromatographed on silica gel [50 g, CHCl3/MeOH (50/1)]

出典と根拠

ORDレコード
ord-10887d57aa234496b30a701643e70b0d
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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