Lithium borohydride → (R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate

HRID 1765636

反応式

HRID 1765636 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([CH2:17][CH2:18][C:19](OC)=[O:20])[C:13](OC)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Li+]>C1COCC1.[Cl-].[Na+].O.O>[OH:20][CH2:19][CH2:18][CH2:17][C@@H:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:13][OH:14]

参加物

6

反応物 2

HCID 4148881Lithium borohydrideHCID 86606597Dimethyl (2R)-2-{[(benzyloxy)carbonyl]amino}pentanedioate

生成物 1

HCID 2757382(R)-Benzyl (1,5-dihydroxypentan-2-yl)carbamate収率 90%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

実験手順

A solution of dimethyl (2R)-2-{[(benzyloxy)carbonyl]amino}pentanedioate (22.4 g) in dry THF (74 ml) was added dropwise over 1 h to a stirred mixture of lithium borohydride (4.5 g) in THF (200 ml) at room temperature, under nitrogen. Stirring at room temperature was continued for 3 days. The reaction mixture was diluted with brine and water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (over magnesium sulphate) and concentrated under reduced pressure to give the title compound (16.5 g) as a white solid.

後処理

  1. extractionextracted with ethyl acetate
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried (over magnesium sulphate)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4fc5996bb36244dc8c309fd9c4e8d29e
出典データセット
uspto-grants-2007_06
特許番号
US07226929B2

関連ノート

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