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Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe) → Methyl 1-({3-[(tert-butoxycarbonyl)amino]-2-phenylpropyl}amino)cyclopentanecarboxylate

HRID 1890721
ノート
印刷プレビュー

反応式

HRID 1890721 の反応式
O=[CH:2][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[NH2:19][C:20]1([C:25]([O:27][CH3:28])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl.C(=O)(O)[O-].[Na+]>[C:8]([O:7][C:6]([NH:5][CH2:4][CH:3]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2][NH:19][C:20]1([C:25]([O:27][CH3:28])=[O:26])[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:12])([CH3:11])([CH3:10])[CH3:9]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 231225Methyl 1-amino-1-cyclopentanecarboxylate (H-Ac5c-OMe)HCID 5049666Sodium triacetoxyborohydrideHCID 11414003tert-Butyl (3-oxo-2-phenylpropyl)carbamate

生成物 1

HCID 58550617Methyl 1-({3-[(tert-butoxycarbonyl)amino]-2-phenylpropyl}amino)cyclopentanecarboxylate

試薬・触媒・溶媒 3

HCID 6212Chloroform溶媒
HCID 6344
Dichloromethane
溶媒
HCID 516892Sodium Bicarbonate溶媒

実験手順

Into a solution of tert-butyl (3-oxo-2-phenylpropyl)carbamate from Step B (0.5 g, 2 mmol) in dry chloroform (20 mL) was added methyl 1-amino-1-cyclopentanecarboxylate (0.431 g, 3.01 mmol). After 15 minutes, sodium triacetoxyborohydride (0.893 g, 4.21 mmol) was added. After 4 hours of stirring at ambient temperature, the reaction mixture was diluted with DCM and 5% sodium bicarbonate. The layers were separated and the aqueous layer was extracted once with DCM. The combined organics were dried over sodium sulfate, filtered, and concentrated in vacuo to yield a residue, which was subjected to a normal phase chromatography, eluting with a gradient of 1-6% methanol in DCM. Concentration of the fractions containing the product provided the title compound. MS: m/z=377 (M+1).

後処理

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted once with DCM
  3. dry with materialThe combined organics were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto yield a residue, which
  7. washeluting with a gradient of 1-6% methanol in DCM
  8. additionConcentration of the fractions containing the product

出典と根拠

ORDレコード
ord-f2c4eb9b3f67496db16af66486442f38
出典データセット
uspto-grants-2013_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08507477B2

反応ノート

読み込み中…

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