Ammonia → 2-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)-N,N-diphenylacetamide

HRID 1608803노트

반응식

HRID 1608803 반응식
[C:1]([CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([N:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:14])[CH2:5]1)#[N:2].N.[H][H]>CO.[Ni]>[NH2:2][CH2:1][CH2:3][C@H:4]1[O:9][C:8]([CH3:11])([CH3:10])[O:7][C@@H:6]([CH2:12][C:13]([N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:14])[CH2:5]1

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 108830131,3-Dioxane-4-acetamide, 6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-, (4R-cis)-(9CI)HCID 178418361HCID 178418361, 화합물2회

생성물 1

HCID 109486112-((4R,6R)-6-(2-aminoethyl)-2,2-dimethyl-1,3-dioxan-4-yl)-N,N-diphenylacetamide수율 95.5%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol용매

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온도
20 °C

실험 절차

A solution of (4R-cis)-6-(cyanomethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide (10.0 g, 0.027 mol) in methanol (150 mL) containing anhydrous ammonia (2.25 g) is reacted with hydrogen gas in a Parr shaker at 30° C. in the presence of a slurry of Raney nickel A-7000 (3.8 g). After 3 hours, uptake of hydrogen has ceased, the mixture is cooled to 20° C., the atmosphere is vented and exchanged for nitrogen, the slurry is filtered through celite, and concentrated at reduced pressure to give 9.5 g of (4R-cis)-6-(2-aminoethyl)-2,2-dimethyl-N,N-diphenyl-1,3-dioxane-4-acetamide as an oil. 1H-NMR (DMSO) δ1.23 (s, 3H), 1.37 (S, 3H), 2.29 (m, 1H), 2.33 (m, 1H), 2.36 (m, 2H), 2.49 (m, 2H), 2.50 (m, 2H), 3.01 (m, 2H), 3.22 (s, 2H), 7.37 (s, 10H).

후처리

  1. filtrationthe slurry is filtered through celite
  2. concentrationconcentrated at reduced pressure

출처 및 근거

ORD 기록
ord-d2c8b69b74de47f4af0c8d63be8f9f66
출처 데이터셋
uspto-grants-1995_03
특허 번호
US05397792

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