Water → (R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol

HRID 913234

반응식

HRID 913234 반응식
[CH2:1]([O:8][CH2:9][C@@H:10]([C:19](ON1C(=O)CCC1=O)=[O:20])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].O>O1CCCC1>[CH2:1]([O:8][CH2:9][C@H:10]([NH:11][C:12](=[O:13])[O:14][C:15]([CH3:17])([CH3:16])[CH3:18])[CH2:19][OH:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 12879025Boc-Ser(Bzl)-OSu

생성물 1

HCID 11065873(R)-(+)-3-Benzyloxy-2-(Boc-amino)-1-propanol수율 104.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under an atmosphere of argon, to a solution of 2,5-dioxopyrrolidin-1-yl O-benzyl-N-t-butoxycarbonyl-L-serinate (4.41 g) in tetrahydrofuran (30 mL) was added sodium borohydride (644 mg) in ice bath and the mixture was stirred at room temperature overnight. Water was added to the reaction solution, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated ammonium chloride solution and brine, dried over anhydrous magnesium sulfate and concentrated to give the title compound (3.30 g) having the following physical data.

후처리

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with an aqueous saturated ammonium chloride solution and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ec1ee1fbaba2488785d377fd24f509c0
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026273B2

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