Lithium Chloride → tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

HRID 345010노트

반응식

HRID 345010 반응식
[CH3:1][C:2]([CH3:20])([O:4][C:5]([NH:7][C@H:8]([C:16](OC)=[O:17])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:6])[CH3:3].[Cl-].[Li+].[BH4-].[Na+]>O1CCCC1.C(O)C>[CH3:3][C:2]([CH3:20])([O:4][C:5]([NH:7][C@@H:8]([CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[CH2:16][OH:17])=[O:6])[CH3:1]

참가 물질

6

반응물 3

HCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 9882138Boc-L-phenylalanine methyl ester

생성물 1

HCID 2733675tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate수율 100%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution containing N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine, methyl ester (10 g, 35.8 mmole) dissolved in a mixture of tetrahydrofuran (190 ml) and absolute ethanol (190 ml) is added lithium chloride (6.09 g, 143.2 mmole). The resulting homogeneous solution is treated with sodium borohydride (5.42 g, 143.2 mmole) and the reaction is stirred at room temperature under argon for 24 hours. The reaction mixture is next filtered using ether (~700 ml) to rinse the filter cake. The resulting filtrate is rinsed with water (3×200 ml) and brine (200 ml), dried over magnesium sulfate, and concentrated in vacuo to give 9 g of crude product. Recrystallization from ether/hexane gives 7.59 g of the title D compound,; m.p. 94°-96°.

후처리

  1. filtrationThe reaction mixture is next filtered
  2. washto rinse the filter cake
  3. washThe resulting filtrate is rinsed with water (3×200 ml) and brine (200 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-089d1eaba0344d5fb0e917683340662d
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05055466

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