Morpholine → Bavisant

HRID 604256노트

반응식

HRID 604256 반응식
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

참가 물질

6

반응물 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

생성물 1

HCID 16061509Bavisant수율 48%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ddc8c3511d2b4348a46192fa9168eb95
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07910582B2

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