Acetic Acid → HCID 53908906, 화합물

HRID 1684087노트

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HRID 1684087 반응식
C([BH3-])#N.[Na+].[F:5][C:6]1[CH:7]=[CH:8][C:9]([O:22][CH3:23])=[C:10]2[C:15]=1[O:14][CH2:13][C@H:12]([NH:16][CH:17]([CH2:20][CH3:21])[CH2:18][CH3:19])[CH2:11]2.[CH:24](=O)[CH2:25][CH3:26].C(O)(=O)C>CO>[F:5][C:6]1[CH:7]=[CH:8][C:9]([O:22][CH3:23])=[C:10]2[C:15]=1[O:14][CH2:13][C@H:12]([N:16]([CH:17]([CH2:18][CH3:19])[CH2:20][CH3:21])[CH2:24][CH2:25][CH3:26])[CH2:11]2

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 527Propanal2회HCID 5003444Sodium cyanoborohydrideHCID 53693748(R)-8-fluoro-5-methoxy-3-(N-3-pentylamino)chroman

생성물 1

HCID 53908906HCID 53908906, 화합물수율 94.4%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Sodiumcyanoborohydride (1.3 g, 20.7 mmol) was added during 10 min. to a stirred solution of (R)-8-fluoro-5-methoxy-3-(N-3-pentylamino)chroman (3.69 g, 13.8 mmol) and propionaldehyde (5 ml, 69.3 mmol) in 100 ml dry MeOH. The pH was adjusted with acetic acid to pH 6. The solution was stirred in room temp. for 18 hours and propionaldehyde (1 ml, 13.7 mmol) was added. After stirring at room temp. for 3.5 hours the solution was concentrated, and the residue was partitionated between 100 ml 2M NH3 and 200 ml ether. Extraction with 2×200 ml ether and drying of the combined organic layers (Na2SO4) gave after evaporation a crude product. Purification by flash chromatography on silica with hexane:acetone 20:1 gave 4.03 g of (R)-8-fluoro-5-methoxy-3-(N-3-pentyl-N-n-propylamino)chroman as an uncolored oil. [α]D22 -83° (c 1.08 in MeOH).

후처리

  1. stirringAfter stirring at room temp. for 3.5 hours the solution
  2. concentrationwas concentrated
  3. extractionExtraction with 2×200 ml ether
  4. dry with materialdrying of the combined organic layers (Na2SO4)
  5. customgave
  6. customafter evaporation a crude product
  7. customPurification by flash chromatography on silica with hexane:acetone 20:1

출처 및 근거

ORD 기록
ord-ef2ccaea214a4344aee8eeb99e2f50fb
출처 데이터셋
uspto-grants-1997_06
특허 번호
US05639772

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