Methanol → (2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidine

HRID 2185488ノート

反応式

HRID 2185488 の反応式
CO.[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:17]([C:27](O)=[O:28])[CH2:16]1)=[O:13])=[O:9])([CH3:6])([CH3:5])[CH3:4].[BH4-].[Li+].O>O1CCCC1>[C:3]([O:7][C:8]([NH:10][CH2:11][C:12]([NH:14][C@H:15]1[CH2:19][N:18]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C@H:17]([CH2:27][OH:28])[CH2:16]1)=[O:13])=[O:9])([CH3:4])([CH3:6])[CH3:5]

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 4148881Lithium borohydrideHCID 21341559trans-4-(N-tert-butoxycarbonylglycyl)amino-N-tert-butoxycarbonyl-L-proline

生成物 1

HCID 70172939(2s,4r)-4-(n-Tert-butoxycarbonylglycylamino)-2-hydroxymethyl-n-tert-butoxycarbonylpyrrolidine収率 97.8%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Methanol (8 mL) was added over a period of 1 hr to a refluxed mixture of trans-4-N-tert-butoxycarbonylglycylamino)-N-tert-butoxycarbonyl-L-proline methyl ester (Compound D103 (B), 1.39 g) and lithium borohydride (328 mg) in tetrahydrofuran (30 mL). After being cooled, water was added to the mixture and the product was extracted twice with chloroform. The combined organic layers were dried over anhydrous sodium sulfate, then evaporated in vacuo and the residue was purified by silica gel column chromatography (chloroform:methanol=95:5, v/v) to give title compound (1.31 g): 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.47 (s, 9H), 1.89 (m, 1H), 1.98 (m, 1H), 3.34 (dd, J=11.7, 3.9 Hz, 1H), 3.60 (d, J=5.9 Hz, 1H), 3.64 (d, J=5.9 Hz, 1H), 3.69 (m, 1H), 3.75 (d, J=5.9 Hz, 1H), 4.04 (m, 1H), 4.42 (m, 1H), 4.55 (m, 1H), 5.15 (m, 1H), and 6.44 (m, 1H).

後処理

  1. temperatureAfter being cooled
  2. extractionthe product was extracted twice with chloroform
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  4. customevaporated in vacuo
  5. customthe residue was purified by silica gel column chromatography (chloroform

出典と根拠

ORDレコード
ord-8081b9b314fd4fe58dfad07b0b181a98
出典データセット
uspto-grants-2002_06
特許番号
US06399629B1

反応ノート

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