Dicyclohexylcarbodiimide → HCID 688299、化合物

HRID 1874644ノート

反応式

HRID 1874644 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:15][CH2:14][CH2:13][C@@H:9]1[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCC(N=C=NC2CCCCC2)CC1.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.Cl.[CH3:51][NH:52][O:53][CH3:54]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:54][O:53][N:52]([CH3:51])[C:10]([C@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:12]

参加物

8

反応物 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

生成物 1

HCID 688299HCID 688299、化合物収率 48.4%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

N-(tert-Butoxycarbonyl)-D-proline (1.505 g, 6.99 mmol), DCC (1.443 g, 6.99 mmol), HOBt (1.071 g, 6.99 mmol), and Hunig's base (2.78 mL, 15.89 mmol) in DCM (31.8 mL) were stirred at room temperature for 1 h. N,O-Dimethylhydroxylamine hydrochloride (0.62 g, 6.36 mmol) and DMAP (0.078 g, 0.636 mmol) were added and the solution stirred at room temperature for 4 h. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel (10%→100% ethyl acetate in hexanes). Obtained (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)pyrrolidine-1-carboxylate (794 mg, 3.07 mmol, 48.4% yield) as a colorless oil. Rotomers (a and b) seen in NMR: 1H NMR (500 MHz, CDCl3) δ 4.52-4.76 (m, 1H), 3.77 (s, 1.5 Ha), 3.71 (s, 1.5 Hb), 3.51-3.64 (m, 1H), 3.33-3.51 (m, 1H), 3.18 (s, 3H), 2.08-2.27 (m, 1H), 1.74-2.04 (m, 3H), 1.45 (s, 4.5 Ha), 1.40 (s, 4.5 Hb); LRMS (ESI) m/e 158.76.

後処理

  1. concentrationThe mixture was concentrated in vacuo
  2. customThe residue was purified by column chromatography on silica gel (10%→100% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-52496683a94c473c874510fec472ddb8
出典データセット
uspto-grants-2012_11
特許番号
US08304577B2

反応ノート

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