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Acetone → (S)-4-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

HRID 1626652
ノート
印刷プレビュー

反応式

HRID 1626652 の反応式
Cl.[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][NH:10][CH2:9][C:7]=2[N:8]=1.C(O)(C(F)(F)F)=O.[CH3:26][C:27]([CH3:29])=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(O)(=O)C>[Cl:2][C:3]1[N:4]=[C:5]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][C@@H:13]2[CH3:18])[C:6]2[CH2:11][N:10]([CH:27]([CH3:29])[CH3:26])[CH2:9][C:7]=2[N:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 86663150(S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine hydrochloride2 回

生成物 1

HCID 86663166(S)-4-(2-chloro-6-isopropyl-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine

試薬・触媒・溶媒 2

HCID 176Acetic Acid触媒
HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of (S)-4-(2-chloro-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidin-4-yl)-3-methylmorpholine (intermediate 6) as a TFA salt (820 mg, 2.0 mmol) in anhydrous THF (5 ml) was added anhydrous acetone (500 μl) and glacial acetic acid (four drops). The reaction was stirred at RT for 30 minutes after which time sodium triacetoxyborohydride (848 mg, 4.0 mmols) was added. After stirring for a further 30 minutes at RT, the reaction was partitioned between water and DCM. The aqueous phase was extracted into DCM and the organic extracts were combined, dried over magnesium sulphate and concentrated in vacuo to afford the title compound as a brown oil, which was used without further purification.

後処理

  1. additionwas added
  2. customthe reaction was partitioned between water and DCM
  3. extractionThe aqueous phase was extracted into DCM
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-987b356a77224a29ac37c05859167b5f
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08785457B2

反応ノート

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