Cyclohexanone → HCID 67343263, 화합물

HRID 1825853노트

반응식

HRID 1825853 반응식
[NH2:1][C@H:2]1[CH2:6][CH2:5][N:4]([C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:8])[CH2:3]1.[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C([BH3-])#N.[Na+]>CO>[CH2:10]([O:9][C:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:1][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:3]1)=[O:8])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

5

반응물 3

HCID 7967CyclohexanoneHCID 1519355(S)-1-Cbz-3-AminopyrrolidineHCID 5003444Sodium cyanoborohydride

생성물 1

HCID 67343263HCID 67343263, 화합물수율 73%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of (3S)-3-amino-pyrrolidine-1-carboxylic acid, benzyl ester (4.40 g, 20 mmol) in methanol (120 mL) was added cyclohexanone (2.75 g, 28 mmol) followed by sodium cyanoborohydride (1.50 g, 24 mmol) at room temprerature. After 3 h, the reaction mixture was concentrated, diluted with dichloromethane (200 mL), washed with aqueous sodium bicarbonate (100 mL), 1 N sodium hydroxide (50 mL), brine (50 mL) and dried (Na2SO4). The crude was purified by flash chromatography using 5% methanol in dichloromethane to give (3S)-3-cyclohexylamino-pyrrolidine-1-carboxylic acid benzyl ester in 73% yield. 1H NMR (300 MHz, CDCl3): in δ 7.36–7.26 (m, 5H), 5.11 (s, 2H), 3.65–3.35 (m, 4H), 3.1–2.95 (m, 1H), 2.5–2.38 (m, 1H), 2.11–1.98 (m, 1H), 1.92–1.54 (m, 5H), 1.31–0.95 (m, 6H); 13C NMR (300 MHz, CDCl3): in δ 154.9, 137.1, 128.4, 127.8, 66.7, 55.0, 54.6, 53.8, 52.6, 44.7, 44.3, 34.1, 32.8, 32.0, 26.1, 25.1; MS (ESI+), 303 (M+H); Rf=1.16.

후처리

  1. concentrationthe reaction mixture was concentrated
  2. additiondiluted with dichloromethane (200 mL)
  3. washwashed with aqueous sodium bicarbonate (100 mL), 1 N sodium hydroxide (50 mL), brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. customThe crude was purified by flash chromatography

출처 및 근거

ORD 기록
ord-54fd923280c44ee7bbef11dc4b5ba12c
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049323B2

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