Sodium triacetoxyborohydride → HCID 178452762, 화합물

HRID 81094노트

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HRID 81094 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

HCID 178452762HCID 178452762, 화합물

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2e2147643ee740edbd6d3d744142f8be
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846657B2

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