Hydrochloric Acid → HCID 57869862, 화합물

HRID 1045663노트

반응식

HRID 1045663 반응식
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[Cl:15][CH2:16][C:17]([NH:19][CH:20]1[C:29](=[O:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:22][CH2:21]1)=[O:18].O.Cl>O1CCCC1>[Cl:15][CH2:16][C:17]([NH:19][C@H:20]1[C@@H:29]([OH:30])[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[O:22][CH2:21]1)=[O:18]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3611392Lithium tri-s-butylborohydrideHCID 57869938HCID 57869938, 화합물

생성물 1

HCID 57869862HCID 57869862, 화합물수율 83%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium tri-sec-butylborohydride (1.0 M solution in tetrahydrofuran, 190 ml, 190 mmol) was added to a solution of 2-chloro-N-(4-oxo-chroman-3-yl)-acetamide (22.6 g, 94.3 mol) in tetrahydrofuran (1000 ml). When the reaction was complete (checked by thin layer chromatography), excess reagent was decomposed by the addition of water and pH was adjusted to 5-6 with 3N aqueous hydrochloric acid. The solution was partitioned between water and chloroform. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform) to afford 2-chloro-N-((3RS,4SR)-cis-4-hydroxychroman-3-yl)-acetamide (19 g, 78.6 mmol, 83%) as white crystals.

후처리

  1. customThe solution was partitioned between water and chloroform
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent; 5-10% methanol in chloroform)

출처 및 근거

ORD 기록
ord-f857c56d53c24578a96b5bf63026b304
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08569294B2

반응 노트

불러오는 중…