Diethyl Ether → HCID 73853093, 화합물

HRID 1245593노트

반응식

HRID 1245593 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])[CH2:15][C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(C1C=CC(S([N:41]=[N+:42]=[N-])(=O)=O)=CC=1)CCCCCCCCCCC.C(N(CC)CC)C.CCOCC>CC#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:19])[C:15](=[N+:41]=[N-:42])[C:16](=[O:18])[CH3:17])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 109151434-Dodecylbenzenesulfonyl azideHCID 21912749tert-Butyl 4-(3-oxobutanoyl)piperidine-1-carboxylate

생성물 1

HCID 73853093HCID 73853093, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A solution of 0.51 g (1.8 mmol) of 1-(tert-butoxycarbonyl)-4-(1,3-dioxo-but-1-yl)piperidine (from Step B) and 0.65 g (1.8 mmol) of para-dodecylbenzenesulfonyl azide (Syn. Comm. 1981, 11, 947–956) in CH3CN at 0° C. was treated with 0.26 mL (1.8 mmol) of triethylamine. The reaction was warmed to rt and stirred for 4.5 hours. The reaction was poured into 100 mL of Et2O and washed with 100 mL of H2O, 100 mL of 2 N HCl and 100 mL of brine. The organic layer was dried over MgSO4 and concentrated. The residue was purified with a 40M Biotage column using 9:1 v/v of hexanes/acetone to afford the title compound as a light yellow oil: RF: 0.33 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.46 (s, 9H), 1.57–1.76 (m, 4H), 2.42 (s, 3H), 2.82 (m, 2H), 3.24 (m, 1H), 4.14 (m, 2H).

후처리

  1. washwashed with 100 mL of H2O, 100 mL of 2 N HCl and 100 mL of brine
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified with a 40M Biotage column

출처 및 근거

ORD 기록
ord-986d0c6234aa46b6ad1b6a02ae87cbc8
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07125887B2

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