Ammonium Hydroxide → HCID 178445772, 화합물

HRID 2404128노트

반응식

HRID 2404128 반응식
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([C:22]#[N:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[OH-]>CO.[Ni]>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:22][NH2:23])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 2

HCID 14923Ammonium HydroxideHCID 178445771HCID 178445771, 화합물

생성물 1

HCID 178445772HCID 178445772, 화합물수율 102.2%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

실험 절차

Compound 6-((trans)-4-tert-butylcyclohexyloxy)-2-naphthonitrile (1.7 g, 5.53 mmol, 1.0 eq.) and NH4OH (0.3 mL, 6.65 mmol, 1.2 eq.) was dissolved in MeOH (5 mL). Then Raney Ni (64 mg, 1.11 mmol, 0.2 eq.) was added to the mixture and the suspension solution was stirred at r.t. under hydrogen atmosphere for 15 h. The mixture was filtrated and purified by silica gel column chromatography using DCM/MeOH (10/1) as eluent to give product as a pale solid (1.76 g, 63%). ESI-MS (M-NH2)+: 295.1. 1H NMR (400 MHz, CDCl3) δ 7.71-7.65 (m, 3H), 7.38 (dd, 1H), 7.15-7.11 (m, 2H), 4.28-4.24 (m, 1H), 3.98 (s, 2H), 2.30-2.26 (m, 2H), 1.91-1.87 (m, 2H), 1.76 (s, 2H), 1.46-1.40 (m, 2H), 1.21-1.12 (m, 3H), 0.90 (s, 9H).

후처리

  1. filtrationThe mixture was filtrated
  2. custompurified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-f27b683393854b4cbb29712de97ff3d3
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08802659B2

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