Morpholine → Bavisant

HRID 912594ノート

反応式

HRID 912594 の反応式
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:28])[C:15]2[CH:20]=[CH:19][C:18]([CH2:21][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[C:29](OC(N1CCN(C(=O)C2C=CC(C=O)=CC=2)CC1)=O)([CH3:32])(C)[CH3:30].N1CCOCC1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CO>[CH:32]1([N:8]2[CH2:13][CH2:12][N:11]([C:14]([C:15]3[CH:20]=[CH:19][C:18]([CH2:21][N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)=[CH:17][CH:16]=3)=[O:28])[CH2:10][CH2:9]2)[CH2:29][CH2:30]1

参加物

6

反応物 4

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 592181854-(4-Morpholin-4-ylmethyl-benzoyl)piperazine-1-carboxylic acid tert-butyl esterHCID 59218188Tert-butyl 4-(4-formylbenzoyl)piperazine-1-carboxylate

生成物 1

HCID 16061509Bavisant収率 48%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

4-(4-Morpholin-4-ylmethyl-benzoyl)-piperazine-1-carboxylic acid tert-butyl ester. A solution of 4-(4-formyl-benzoyl)piperazine-1-carboxylic acid tert-butyl ester (2.06 g) in methanol (100 mL) was treated with morpholine (4 mL) and NaB(OAc)3H (6.98 g, in portions over 1 h). After 3 h, the mixture was diluted with satd. aq. NaHCO3 and extracted with CH2Cl2. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2) to give the title compound (1.22 g, 48%). MS (ESI): mass calcd. for C21H31N3O4, 389.23; m/z found, 390.4 [M+H]+. 1H NMR (CDCl3): 7.39-7.33 (m, 4H), 3.75-3.66 (m, 6H), 3.50 (s, 2H), 3.51-3.33 (m, 6H), 2.45-2.41 (m, 4H), 1.46 (s, 9H).

後処理

  1. additionthe mixture was diluted with satd
  2. extractionaq. NaHCO3 and extracted with CH2Cl2
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2)

出典と根拠

ORDレコード
ord-1441d4880ac742a6969a00fca52b90c6
出典データセット
uspto-grants-2011_09
特許番号
US08026242B2

反応ノート

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