Acetic Acid → HCID 53908906、化合物

HRID 37672ノート

反応式

HRID 37672 の反応式
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

参加物

6

反応物 4

HCID 176Acetic AcidHCID 527Propanal2 回HCID 5003444Sodium cyanoborohydrideHCID 53693748(R)-8-fluoro-5-methoxy-3-(N-3-pentylamino)chroman

生成物 1

HCID 53908906HCID 53908906、化合物収率 94.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-adc6483939c74918967bea1dad101c89
出典データセット
uspto-grants-1995_05
特許番号
US05420151

反応ノート

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