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

HRID 1719301ノート

反応式

HRID 1719301 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-e09d5ec578b54016b7ea84daf26efee6
出典データセット
uspto-grants-1985_09
特許番号
US04539152

反応ノート

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