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Sodium borohydride → Tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate

HRID 1499911
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HRID 1499911 반응식
[C:1]([C:4]1[C:5]([O:24][CH3:25])=[C:6]([CH:13]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[C:7]([C:11]#[N:12])=[C:8]([CH3:10])[CH:9]=1)(=[O:3])[CH3:2].[BH4-].[Na+]>CO.C(OCC)(=O)C.O>[C:11]([C:7]1[C:8]([CH3:10])=[CH:9][C:4]([CH:1]([OH:3])[CH3:2])=[C:5]([O:24][CH3:25])[C:6]=1[CH:13]1[CH2:14][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:16]1)#[N:12]
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참가 물질

6

반응물 2

HCID 4311764Sodium borohydrideHCID 86677831Tert-butyl 3-(3-acetyl-6-cyano-2-methoxy-5-methylphenyl)azetidine-1-carboxylate

생성물 1

HCID 86677832Tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate수율 99%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매
HCID 8857
Ethyl Acetate
용매

실험 절차

The tert-butyl 3-(3-acetyl-6-cyano-2-methoxy-5-methylphenyl)azetidine-1-carboxylate (2.2 g, 6.4 mmol) was dissolved in methanol (20 mL) and cooled in ice bath. The sodium tetrahydroborate (0.26 g, 7.0 mmol) was added portionwise and the reaction was monitored by LC/MS. After stirring for 1 h the reaction was complete. This was diluted with ethyl acetate and water. The combined organic layer was washed with water, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated to give crude tert-butyl 3-[2-cyano-5-(1-hydroxyethyl)-6-methoxy-3-methylphenyl]azetidine-1-carboxylate as a yellow foam (2.1 g, 99%). LCMS calculated for C15H19N2O4(M+H)+: m/z=291.1; found: 291.1.

후처리

  1. temperaturecooled in ice bath
  2. washThe combined organic layer was washed with water, saturated sodium bicarbonate, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-5482fb0c20b5415382dde7b996802624
출처 데이터셋
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09199982B2

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