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 1965170ノート

反応式

HRID 1965170 の反応式
[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

参加物

8

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 111,2-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-14b4e26602b34fec8148d5a8fdc38bd6
出典データセット
uspto-grants-2013_04
特許番号
US08415486B2

反応ノート

読み込み中…