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

HRID 345010ノート

反応式

HRID 345010 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-089d1eaba0344d5fb0e917683340662d
出典データセット
uspto-grants-1991_10
特許番号
US05055466

反応ノート

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