Acetic Acid → 1-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate

HRID 2233944ノート

反応式

HRID 2233944 の反応式
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]1[CH2:8][C@@H:7](O)[CH2:6][N:5]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11].Cl.[Cl:19][C:20]1[C:24]([Cl:25])=[C:23]([CH3:26])[NH:22][C:21]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)=[O:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl.CCOCC>[Cl:19][C:20]1[C:24]([Cl:25])=[C:23]([CH3:26])[NH:22][C:21]=1[C:27]([NH:29][CH:30]1[CH2:35][CH2:34][N:33]([CH:7]2[CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:4]([C:3]([O:2][CH3:1])=[O:17])[CH2:8]2)[CH2:32][CH2:31]1)=[O:28]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl esterHCID 5049666Sodium triacetoxyborohydrideHCID 68579996HCID 68579996、化合物2 回

生成物 1

HCID 866082951-tert-Butyl 2-methyl (2S)-4-(4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}piperidin-1-yl)pyrrolidine-1,2-dicarboxylate

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 3283Diethyl Ether溶媒

実験手順

N-BOC-trans-4-Hydroxy-L-proline methylester (0.20 g, 0.81 mM) and 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide (free base of Intermediate 1), 0.16 g, 0.81 mM) were stirred in 1,2-dichloroethane (3.5 ml). Sodium triacetoxyborohydride (0.24 g, 1.1 mM) was added followed by acetic acid (0.05 ml). The reaction was stirred under nitrogen at room temperature overnight then diluted with ether and washed with 1 N sodium hydroxide. The organic phase was washed with brine, dried over MgSO4 and concentrated to give an orange oil. The oil was chromatographed using EtOAc to give the desired product as a light yellow solid.

後処理

  1. washwashed with 1 N sodium hydroxide
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customto give an orange oil
  6. customThe oil was chromatographed

出典と根拠

ORDレコード
ord-3f684d12d6864294a450c20e06ae6240
出典データセット
uspto-grants-2010_05
特許番号
US07709503B2

反応ノート

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