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

HRID 82403ノート

反応式

HRID 82403 の反応式
O[Li].O.[CH3:4][C@H:5]1[C:13]2[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)=[N:11][CH:10]=[N:9][C:8]=2[C@H:7]([O:27]C(=O)C2C=CC([N+]([O-])=O)=CC=2)[CH2:6]1.C1COCC1>O>[OH:27][C@H:7]1[C:8]2[N:9]=[CH:10][N:11]=[C:12]([N:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[C:13]=2[C@H:5]([CH3:4])[CH2:6]1

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59580346tert-butyl 4-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate

生成物 1

HCID 59580343tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

LiOH—H2O (0.499 g, 11.9 mmol) was added to a 0° C. solution of tert-butyl 4-((5R,7R)-5-methyl-7-(4-nitrobenzoyloxy)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (2.30 g, 4.76 mmol) in 2:1 THF:H2O (40 mL). The reaction mixture was warmed to room temperature and stirred for 1 hour. The THF was removed by rotary evaporation, and saturated NaHCO3 was added. The mixture was extracted with ethyl acetate. The combined extracts were washed with saturated NaHCO3 (1×), dried (Na2SO4), filtered, and concentrated to give tert-butyl 4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate (1.59 g, 100.0% yield) as a yellow foam. LC/MS (APCI+) m/z 335 [M+H]+. The tert-butyl 4-((5R,7S)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazine-1-carboxylate was prepared using a analogous method.

後処理

  1. customThe THF was removed by rotary evaporation, and saturated NaHCO3
  2. additionwas added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe combined extracts were washed with saturated NaHCO3 (1×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-5c83b6ba9a584a40802ce6127407b4c4
出典データセット
uspto-grants-2014_09
特許番号
US08846681B2

反応ノート

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