Acetic Acid → {1-[6-(3,4-Difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester

HRID 1965170노트

반응식

HRID 1965170 반응식
[CH2:1]([O:8][C:9](=[O:35])[NH:10][CH:11]([C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[NH:23][CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:36]1[CH2:41][CH2:40][C:39](=O)[CH2:38][CH2:37]1.CC(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.CCOC(C)=O>[CH2:1]([O:8][C:9](=[O:35])[NH:10][CH:11]([C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[NH:23][CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:1]([O:8][C:9](=[O:35])[NH:10][CH:11]([C:16]([N:18]1[CH2:22][CH2:21][CH:20]2[N:23]([CH:39]3[CH2:40][CH2:41][O:36][CH2:37][CH2:38]3)[CH2:24][CH:25]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[C:29]([F:34])[CH:28]=3)[CH:19]12)=[O:17])[C:12]([CH3:15])([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 67608719{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester

생성물 2

HCID 67607614{1-[6-(3,4-Difluoro-phenoxy)-4-(tetrahydro-pyran-4-yl)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl esterHCID 67608719{1-[6-(3,4-Difluoro-phenoxy)-hexahydro-pyrrolo[3,2-b]pyrrole-1-carbonyl]-2,2-dimethyl-propyl}-carbamic acid benzyl ester

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

Secondary amine 24 (200 mg, 0.41 mmol) was dissolved in 1,2-dichloroethane (4 mL) at ambient temperature and tetrahydro-4H-pyran-4-one (84 μL, 0.90 mmol), HOAc (50 μL, 0.82 mmol), and sodium triacetoxyborohydride (172 mg, 0.78 mmol) were added. After 12 h, the reaction mixture was diluted with EtOAc, washed successively with saturated aqueous NaHCO3 (3×), and brine, dried over anhydrous Na2SO4, filtered, and concentrated. The crude orange mixture was purified by reverse-phase HPLC (2″ Dynamax® C18, 10-100% ACN/water containing 0.1% HOAc over 25 min; Flow: 40 mL/min) to give 100 mg of 24 and 90 mg of 25 as a colorless oil. Mass spectrum, m/z [572.0] (M+H)+.

후처리

  1. washwashed successively with saturated aqueous NaHCO3 (3×), and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude orange mixture was purified by reverse-phase HPLC (2″ Dynamax® C18, 10-100% ACN/water containing 0.1% HOAc over 25 min

출처 및 근거

ORD 기록
ord-14b4e26602b34fec8148d5a8fdc38bd6
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08415486B2

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