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

HRID 1180977

反応式

HRID 1180977 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-381345f6c75f434daaa612f4f1d43cdb
出典データセット
uspto-grants-2007_10
特許番号
US07282497B2

関連ノート

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