Ammonium formate → Compound 18

HRID 722402ノート

反応式

HRID 722402 の反応式
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][C@@H:16]([C:18]3[CH:32]=[CH:31][C:21]([O:22][CH2:23][C@@H:24]([N:26]4[CH2:30][CH2:29][CH2:28][CH2:27]4)[CH3:25])=[CH:20][CH:19]=3)[C@@H:15]([C:33]3[CH:38]=[CH:37][C:36]([O:39][Si](C(C)C)(C(C)C)C(C)C)=[CH:35][CH:34]=3)[S:14][C:13]=2[CH:50]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CCO.CCOC(C)=O.O.[Pd]>[OH:39][C:36]1[CH:37]=[CH:38][C:33]([C@H:15]2[S:14][C:13]3[CH:50]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=3[O:17][C@H:16]2[C:18]2[CH:32]=[CH:31][C:21]([O:22][CH2:23][C@@H:24]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[CH3:25])=[CH:20][CH:19]=2)=[CH:34][CH:35]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 587430611-{(1S)-2-[4-((2S,3R)-6-(benzyloxy)-3-{4-[(triisopropylsilyl)oxy]phenyl}-2,3-dihydro-1,4-benzoxathiin-2-yl)phenoxy]-1-methylethyl}pyrolidine

生成物 1

HCID 449208Compound 18

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 86601158Ethanol ethyl acetate water溶媒

反応条件

温度
80 °C

実験手順

A stirred mixture of 102 mg (0.14 mmol) of compound 10a, generated in Example 10, Step A, 30.6 mg (0.29 mmol) of palladium black and 181.2 mg (0.29 mmol) ammonium formate in 3 mL of EtOH/EtOAc/H2O (7:2:1) was heated at 80° C. for 2 h. The reaction mixture was filtered through a pad of Celite® to remove the catalyst, washed thoroughly with EtOH/EtOAc/H2O (7:2:1), and the filtrate was partitioned between water and EtOAc. The organic phase was separated, dried over Na2SO4, filtered, evaporated, and dried in vacuo to give the crude product which was used without purification.

後処理

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. customto remove the catalyst
  3. washwashed thoroughly with EtOH/EtOAc/H2O (7:2:1)
  4. customthe filtrate was partitioned between water and EtOAc
  5. customThe organic phase was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-1ce3b14e8f5048ebb4648f2a35f88b26
出典データセット
uspto-grants-2006_11
特許番号
US07138426B2

反応ノート

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