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Sodium borohydride → HCID 53924158, 화합물

HRID 1459401
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HRID 1459401 반응식
C[O:2][C:3](=O)[C:4]([CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)([CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].[BH4-].[Na+]>CO>[C:8]12([NH:7][C:5](=[O:6])[C:4]([CH2:3][OH:2])([CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:16]3)[CH2:15]1)[CH2:17]2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 57147682HCID 57147682, 화합물

생성물 1

HCID 53924158HCID 53924158, 화합물수율 57.3%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a well-stirred solution of N-adamantan-1-yl-2,2-bis-pyridin4-ylmethyl-malonamic acid methyl ester (14.92 g, 34 mmol) in methanol (175 ml), sodium borohydride (6.50 g, 172 mmol) was added portionwise over 1 hour (ambient temperature). After stirring at ambient temperature for 18 hours, the solvent was removed in vacuo, and the residue was extracted with aqueous sodium bicarbonate/chloroform (300 ml of each). The aqueous layer was then extracted three times with equal volumes of chloroform. The combined organic extracts were concentrated in vacuo to an oil (13.55 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/chloroform=4:96 in volume) afforded the (free base) title compound as an oil (7.9 g).

후처리

  1. customthe solvent was removed in vacuo
  2. extractionthe residue was extracted with aqueous sodium bicarbonate/chloroform (300 ml of each)
  3. extractionThe aqueous layer was then extracted three times with equal volumes of chloroform
  4. concentrationThe combined organic extracts were concentrated in vacuo to an oil (13.55 g)
  5. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/chloroform=4:96 in volume)

출처 및 근거

ORD 기록
ord-9bcd65ce0d7b4f698a606ece0a63d5b7
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05854232

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