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

HRID 2185488노트

반응식

HRID 2185488 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8081b9b314fd4fe58dfad07b0b181a98
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06399629B1

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