Acetic Acid → HCID 67999092, 화합물

HRID 932156노트

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HRID 932156 반응식
[CH2:1]([C@@:4]1([CH3:30])[CH2:9][C@H:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=2)[C@@H:7]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[N:6]([C@@H:24]([CH2:27][CH3:28])[CH:25]=O)[C:5]1=[O:29])[CH:2]=[CH2:3].[C@@H:31]12[CH2:37][C@@H:34]([NH:35][CH2:36]1)[CH2:33][O:32]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>ClCCCl>[C@@H:31]12[CH2:37][C@@H:34]([N:35]([CH2:25][C@@H:24]([N:6]3[C@H:7]([C:17]4[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=4)[C@@H:8]([C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([Cl:16])[CH:11]=4)[CH2:9][C@@:4]([CH2:1][CH:2]=[CH2:3])([CH3:30])[C:5]3=[O:29])[CH2:27][CH3:28])[CH2:36]1)[CH2:33][O:32]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 42554306(1R,4R)-2-Oxa-5-azabicyclo[2.2.1]heptaneHCID 58573909(S)-2-((3S,5R,6S)-3-Allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanal

생성물 1

HCID 67999092HCID 67999092, 화합물

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

To a solution of (S)-2-((3S,5R,6S)-3-allyl-5-(3-chlorophenyl)-6-(4-chlorophenyl)-3-methyl-2-oxopiperidin-1-yl)butanal (100 mg, 0.224 mmol; Example 91, Step C) in DCE (2 mL) was added (1R,4R)-2-oxa-5-azabicyclo[2.2.1]heptane (Butora, G.; Goble, S.; Pastemak, A.; Yang, L.; Zhou, C.; Moyes, C. U.S. Patent Publication No. 2008/0081803 (50 mg, 0.504 mmol) followed by sodium triacetoxyborohydride (95 mg, 0.448 mmol) and acetic acid (1.2 μL, 0.022 mmol). After stirring overnight, the mixture was quenched with sat. aq. NaHCO3 solution. The mixture was extracted with ethyl acetate (2×). The combined organic layers were washed with sat. aq. NaCl solution, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography on silica gel (eluent: 1 to 5% methanol/dichloromethane) to afford the title compound.

후처리

  1. customthe mixture was quenched with sat. aq. NaHCO3 solution
  2. extractionThe mixture was extracted with ethyl acetate (2×)
  3. washThe combined organic layers were washed with sat. aq. NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 1 to 5% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-b9ef9ada479c4e3186e7844efc006252
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296736B2

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