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

HRID 749291

反応式

HRID 749291 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2eb114e2653d4ba2a97f905faf0e9425
出典データセット
uspto-grants-2008_07
特許番号
US07402605B2

関連ノート

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