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Sodium triacetoxyborohydride → (4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate

HRID 736781
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HRID 736781 반응식
[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[C:7](=[N:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:6][CH2:5][O:4][CH2:3]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(#N)C.C(O)(=O)C>[CH3:1][C:2]1([C:17]([O:19][CH3:20])=[O:18])[C@H:7]([NH:8][C@@H:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[CH2:6][CH2:5][O:4][CH2:3]1
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HCID 5049666Sodium triacetoxyborohydrideHCID 68817214Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate

생성물 1

HCID 68821088(4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate수율 37%

시약·촉매·용매 1

HCID 22391770Acetonitrile aceticacid용매

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온도
0 °C

실험 절차

Methyl 3-methyl-4-((R)-1-phenylethylimino)-tetrahydro-2H-pyran-3-carboxylate (crude, 13.53 mmol) in acetonitrile-acetic acid (1:1, 80 mL) was treated with NaBH(OAc)3 and stirred for 2.5 h at 0° C. Following concentration in vacuo, the residue was dissolved in ethyl acetate (200 mL), washed with saturated NaHCO3 until the aqueous phase was basic, dried over MgSO4, and purified by chromatography with 20% ethyl acetate/hexane to yield 1.37 g (37% in 2 steps) of (4R)-methyl 3-methyl-4-((R)-1-phenylethylamino)-tetrahydro-2H-pyran-3-carboxylate. MS: (M+H)+=278.1.

후처리

  1. concentrationconcentration in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  3. washwashed with saturated NaHCO3 until the aqueous phase
  4. dry with materialdried over MgSO4
  5. custompurified by chromatography with 20% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-161aeb6776734943aef6828f9a26e91b
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07595327B2

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