Hydrochloric Acid → 1-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-5-phenyl-, 1,1-dimethylethyl ester, (2S,5R)-

HRID 354439ノート

反応式

HRID 354439 の反応式
[C:1]([N:8]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C@H:9]1[C:10](O)=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].S(C)C.Cl>C1COCC1>[C:1]([N:8]1[C@@H:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:14][CH2:13][C@H:9]1[CH2:10][OH:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 2755972(2S,5R)-1-[(tert-butoxy)carbonyl]-5-phenylpyrrolidine-2-carboxylic acid

生成物 1

HCID 207378581-Pyrrolidinecarboxylic acid, 2-(hydroxymethyl)-5-phenyl-, 1,1-dimethylethyl ester, (2S,5R)-収率 102.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of N-Boc-5-(R)-phenyl-(2S)-proline (1.14 g, 3.91 mmol) in THF (20 ml) was added 10M-BH3.Me2S (780 ml, 7.82 mmol) at rt, and the resulting mixture was heated under reflux for 30 min. The mixture was poured into aq. 1N-HCl and extracted with EtOAc. The organic layer was dried over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with CHCl3—MeOH (10:1) as eluent to give N-Boc-2-(S)-hydroxymethyl-5-(R)-phenylpyrrolidine (1.11 g, quant.) as a colorless oil: 1H-NMR (CDCl3) δ1.19 (brs, 9 H), 1.65 (brs, 1 H), 1.83-1.90 (m, 1 H), 1.98-2.06 (m, 1 H), 2.22-2.31 (m, 1 H), 3.75-3.86 (m, 2 H), 4.16-4.19 (m, 1 H), 4.83 (t, J=6.8 Hz, 1 H), 4.89 (brs, 1 H), 7.19-7.31 (m, 5 H); MS (ESI) m/z, 2.78 (M++H).

後処理

  1. temperatureunder reflux for 30 min
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel with CHCl3—MeOH (10:1) as eluent

出典と根拠

ORDレコード
ord-c12a60d6ff3543b08f3bb6f068bb7f20
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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