Sodium borohydride → (3R,4R)-4-(2-hydroxyethyl)-3-phthalimidoazetidin-2-one

HRID 1719301노트

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HRID 1719301 반응식
[O:1]=[CH:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@@H:5]1[N:9]1[C:13](=[O:14])[C:12]2=[CH:15][CH:16]=[CH:17][CH:18]=[C:11]2[C:10]1=[O:19].[BH4-].[Na+]>CO.ClCCl>[OH:1][CH2:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@@H:5]1[N:9]1[C:10](=[O:19])[C:11]2=[CH:18][CH:17]=[CH:16][CH:15]=[C:12]2[C:13]1=[O:14]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 53769960(3R,4R)-4-(2-oxoethyl)-3-phthalimido-2-oxoazetidine

생성물 1

HCID 53834571(3R,4R)-4-(2-hydroxyethyl)-3-phthalimidoazetidin-2-one수율 51.5%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 6344Dichloromethane용매

실험 절차

To a solution of (3R,4R)-4-(2-oxoethyl)-3-phthalimidoazetidin-2-one (52 mg) in a mixture of methanol (3ml) and dichloromethane (1 ml) was added a solution of sodium borohydride (8 mg) in methanol (2 ml) at 0° C. during one hour. The reaction was quenched by addition of acetic acid (two drops). After evaporation in vacuo, the residue was chromatographed on silica gel (1.6 g; eluting with 3 to 5% methanol in dichloromethane) to give 32 mg of crude crystals. Crystallization from a mixture of methanol and ether afforded 27 mg(51.5%) of (3R,4R)-4-(2-hydroxyethyl)-3-phthalimidoazetidin-2-one. IR (Nujol): 3350(br), 3250, 1750, and 1705 cm-1 ; NMR (DMSO-d6) δ: 1.79 (q, J=6 Hz, 2H), 3.46 (m, 2H), 3.97 (dt, J=2.5 and 6 Hz, 1H), 4.47 (brs, 1H), 4.89 (d, J=2.5 Hz, 1H), 7.86 (s, 4H), and 8.42 (brs, 1H).

후처리

  1. customThe reaction was quenched by addition of acetic acid (two drops)
  2. customAfter evaporation in vacuo
  3. customthe residue was chromatographed on silica gel (1.6 g; eluting with 3 to 5% methanol in dichloromethane)
  4. customto give 32 mg of crude crystals
  5. customCrystallization
  6. additionfrom a mixture of methanol and ether

출처 및 근거

ORD 기록
ord-e09d5ec578b54016b7ea84daf26efee6
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539152

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