Acetic Anhydride → (R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate

HRID 75399ノート

反応式

HRID 75399 の反応式
[CH3:1][C:2]([O:4][C:5]([CH3:7])=[O:6])=O.[C:8]([O:12][C:13]([N:15]1[CH2:20][CH2:19][N:18]([C:21]2[N:26]=[CH:25][N+:24]([O-])=[C:23]3C[CH2:29][C@@H:30](C)[C:22]=23)[CH2:17][CH2:16]1)=[O:14])([CH3:11])([CH3:10])[CH3:9]>>[C:5]([O:4][CH:2]1[C:23]2[N:24]=[CH:25][N:26]=[C:21]([N:18]3[CH2:19][CH2:20][N:15]([C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[CH2:16][CH2:17]3)[C:22]=2[C@H:30]([CH3:29])[CH2:1]1)(=[O:6])[CH3:7]

参加物

3

反応物 2

HCID 7918Acetic AnhydrideHCID 67338667(R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide

生成物 1

HCID 59580360(R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate収率 100%

反応条件

温度
90 °C

実験手順

Ac2O (77.0 mL, 816 mmol) was added to (R)-4-(4-(tert-butoxycarbonyl)piperazin-1-yl)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine 1-oxide (21.0 g, 62.8 mmol). The reaction mixture was heated under nitrogen in a 90° C. sand bath and stirred for 100 minutes. The reaction mixture was cooled to room temperature, and excess acetic anhydride was removed by rotary evaporation. The resulting oil was dissolved in DCM, which was then poured carefully into ice saturated Na2CO3. The mixture was extracted with DCM, and the combined extracts were dried (Na2SO4), filtered and concentrated to give (5R)-tert-butyl 4-(7-acetoxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (23.6 g, 100%) as a foam. LC/MS (APCI+) m/z 377.1 [M+H]+.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customexcess acetic anhydride was removed by rotary evaporation
  3. dissolutionThe resulting oil was dissolved in DCM
  4. additionwhich was then poured carefully into ice saturated Na2CO3
  5. extractionThe mixture was extracted with DCM
  6. dry with materialthe combined extracts were dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-c3f30c1b909a42d39923a72f673ca86e
出典データセット
uspto-grants-2014_09
特許番号
US08835434B2

反応ノート

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