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Lithium borohydride → (2-{[(4-Cyano-2-hydroxymethyl-benzyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester

HRID 1592646
ノート
印刷プレビュー

反応式

HRID 1592646 の反応式
C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH2:12][N:13]([CH2:22][C:23]1[C:28]([NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[CH:27][CH:26]=[CH:25][N:24]=1)[CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=1.[Li+].[BH4-]>CO>[C:33]([O:32][C:30](=[O:31])[NH:29][C:28]1[C:23]([CH2:22][N:13]([CH2:12][C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[CH2:3][OH:2])[CH2:14][C:15]2[C:20]([CH3:21])=[CH:19][CH:18]=[CH:17][N:16]=2)=[N:24][CH:25]=[CH:26][CH:27]=1)([CH3:36])([CH3:34])[CH3:35]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 4148881Lithium borohydrideHCID 672728132-{[(3-tert-Butoxycarbonylamino-pyridin-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester

生成物 1

HCID 67272411(2-{[(4-Cyano-2-hydroxymethyl-benzyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester収率 98.7%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a cold (0° C.) solution of 2-{[(3-tert-Butoxycarbonylamino-pyridin-2-ylmethyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-5-cyano-benzoic acid methyl ester (0.388 g, 0.77 mmol) in MeOH (7 mL) was added LiBH4 (107 mg, 4.91 mmol) and the mixture was allowed to warm to room temperature overnight. The mixture was concentrated and the residue was partitioned between CH2Cl2 (50 mL) and 1.0 N NaOH (15 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (3×15 mL). The combined organic extracts were dried (Na2SO4) and concentrated and provided 0.36 g of (2-{[(4-Cyano-2-hydroxymethyl-benzyl)-(3-methyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-carbamic acid tert-butyl ester as a white solid, which was used without further purification.

後処理

  1. concentrationThe mixture was concentrated
  2. customthe residue was partitioned between CH2Cl2 (50 mL) and 1.0 N NaOH (15 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with CH2Cl2 (3×15 mL)
  5. dry with materialThe combined organic extracts were dried (Na2SO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-918be09755cb4b6db075294f19becc5f
出典データセット
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07291631B2

反応ノート

読み込み中…

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