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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sodium triacetoxyborohydride → 1,1-dimethylethyl {(3R,4S)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-3-hydroxy-4-piperidinyl}carbamate

HRID 656974
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HRID 656974 반응식
CO[CH:3](O)[CH2:4][N:5]1[C:14]2[C:9](=[N:10][CH:11]=[C:12]([F:15])[CH:13]=2)[CH:8]=[CH:7][C:6]1=[O:16].CC(N([C@H]1CCNC[C@H]1O)C(=O)[O-])(C)C.[C:33]([O:37][C:38](=[O:47])[NH:39][C@H:40]1[CH2:45][CH2:44][NH:43][CH2:42][C@H:41]1[OH:46])([CH3:36])([CH3:35])[CH3:34].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.CO>[F:15][C:12]1[CH:13]=[C:14]2[C:9]([CH:8]=[CH:7][C:6](=[O:16])[N:5]2[CH2:4][CH2:3][N:43]2[CH2:44][CH2:45][C@H:40]([NH:39][C:38](=[O:47])[O:37][C:33]([CH3:34])([CH3:35])[CH3:36])[C@H:41]([OH:46])[CH2:42]2)=[N:10][CH:11]=1
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참가 물질

7

반응물 4

HCID 5049666Sodium triacetoxyborohydrideHCID 578152967-fluoro-1-(2-hydroxy-2-methoxyethyl)-1,5-naphthyridin-2(1H)-oneHCID 67426921tert-butyl N-[(3R,4S)-3-hydroxypiperidin-4-yl]carbamateHCID 866230711,1-dimethylethyl[(3R,4S)-3-hydroxy-4-piperidinyl]carbamate

생성물 1

HCID 585793371,1-dimethylethyl {(3R,4S)-1-[2-(7-fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)ethyl]-3-hydroxy-4-piperidinyl}carbamate

시약·촉매·용매 2

HCID 887Methanol용매HCID 6212Chloroform용매

실험 절차

(7-Fluoro-2-oxo-1,5-naphthyridin-1(2H)-yl)acetaldehyde methyl hemiacetal (200 mg, 0.8396 mmol) and 1,1-dimethylethyl[(3R,4S)-3-hydroxy-4-piperidinyl]carbamate (for a synthesis see WO2004058144, Example 5(c), cis-(3-hydroxy-piperidin-4-yl)-carbamic acid tert-butyl ester Enantiomer 1) (182 mg, 1 eq.) were stirred in chloroform (10 ml) plus MeOH (0.5 ml) under argon for 2 hours. Sodium triacetoxyborohydride (534 mg, 3 eq.) was added in one portion and the mixture was stirred at rt overnight, then quenched by addition of saturated aqueous sodium hydrogen cabonate (20 ml) and extracted with 20% v:v MeOH in DCM (3×200 ml). The organic extractes were combined, dried over anhydrous magnesium sulphate, filtered and evaporated under reduced pressure to give the crude product, which was purified by column chromatography on silica, eluted with 0-20% (2M ammonia in MeOH) in DCM. Appropriate fractions were combined and evaporated under reduced pressure to give title compound (247 mg) as an off-white foam.

후처리

  1. customquenched by addition of saturated aqueous sodium hydrogen cabonate (20 ml)
  2. extractionextracted with 20% v
  3. dry with materialdried over anhydrous magnesium sulphate
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customto give the crude product, which
  7. customwas purified by column chromatography on silica
  8. washeluted with 0-20% (2M ammonia in MeOH) in DCM
  9. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d986d71f251d42338241d59b5628c95f
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08071592B2

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