Sodium triacetoxyborohydride → HCID 178452762、化合物

HRID 81094ノート

反応式

HRID 81094 の反応式
[NH2:1][C:2]1[C:3]([Cl:17])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH:25]=O)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:17][C:3]1[C:2]([NH:1][CH2:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]2)=[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:6]=[C:5]([Cl:16])[N:4]=1

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86724467Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamateHCID 178461263HCID 178461263、化合物

生成物 1

HCID 178452762HCID 178452762、化合物

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate (353 g, 1.27 mol) and trans-4-methylcyclohexanecarbaldehyde (160 g, 1.27 mol) in DCM (8.0 L) and acetic acid (2 ml) was added sodium triacetoxyborohydride (807.7 g, 3.81 mol) at 0° C. The mixture was stirred for 15 min, and then warmed to room temperature. The mixture was stirred for 15 h at room temperature and then quenched with water (10 L). The mixture was filtered, the filtrate was separated, and the organic layer was concentrated under reduced pressure to give crude product. The crude product was purified over a silica gel column, eluting with EtOAc: petroleum ether (0-1:10), to give tert-butyl (2,6-dichloro-3-(((trans-4-methylcyclohexyl)methyl)amino)pyridin-4-yl)carbamate.

後処理

  1. stirringThe mixture was stirred for 15 h at room temperature
  2. customquenched with water (10 L)
  3. filtrationThe mixture was filtered
  4. customthe filtrate was separated
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customto give crude product
  7. customThe crude product was purified over a silica gel column
  8. washeluting with EtOAc: petroleum ether (0-1:10)

出典と根拠

ORDレコード
ord-2e2147643ee740edbd6d3d744142f8be
出典データセット
uspto-grants-2014_09
特許番号
US08846657B2

反応ノート

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