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Hydrochloric Acid → (2R,5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one

HRID 626914
ノート
印刷プレビュー

反応式

HRID 626914 の反応式
Cl.[CH3:2][N:3]1[CH2:27][CH2:26][C@:5]2([N:9]=[C:8]([C:10]3[N:15]=[C:14]([C:16]4[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=4)[CH:13]=[CH:12][N:11]=3)[CH2:7][CH2:6]2)[C:4]1=[O:28].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH3:2][N:3]1[CH2:27][CH2:26][C@:5]2([NH:9][C@@H:8]([C:10]3[N:15]=[C:14]([C:16]4[CH:17]=[CH:18][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:20][CH:21]=4)[CH:13]=[CH:12][N:11]=3)[CH2:7][CH2:6]2)[C:4]1=[O:28]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 5049666Sodium triacetoxyborohydrideHCID 90015084(5S)-7-Methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]non-1-en-6-one

生成物 1

HCID 72548327(2R,5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one収率 21.5%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

Concentrated aq. HCl (71.99 μL, 0.84 mmol) was added to a solution of (5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]non-1-en-6-one (which may be prepared as described in Description 9) (314 mg, 0.84 mmol) in DCM (10 mL) at 0° C. Sodium triacetoxyborohydride (533.3 mg, 2.52 mmol) was added in a single portion and the resulting mixture was stirred allowing warming to room temperature. After 90 minutes the reaction was quenched by the addition of sat. aq. Na2CO3 and the resultant mixture was filtered. The phases were separated, the organic layer was dried (Na2SO4) and the solvent was evaporated to afford a brown oil. This was purified using a Biotage SP4 with a 25 g SNAP cartridge, eluting with 0 to 20% MeOH in EtOAc. This gave two products; the first to elute: (2R,5S)-7-methyl-2-[4-[4-(trifluoromethyl)phenyl]pyrimidin-2-yl]-1,7-diazaspiro[4.4]nonan-6-one (68 mg, 0.1807 mmol, 21.5% yield) was obtained as a yellow oil.

後処理

  1. customAfter 90 minutes the reaction was quenched by the addition of sat. aq. Na2CO3
  2. filtrationthe resultant mixture was filtered
  3. customThe phases were separated
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. customthe solvent was evaporated
  6. customto afford a brown oil
  7. customThis was purified
  8. washeluting with 0 to 20% MeOH in EtOAc
  9. customThis gave two products
  10. washthe first to elute

出典と根拠

ORDレコード
ord-5b25ad2af92f4fa6b75d041dd9057632
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309254B2

反応ノート

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