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

HRID 851396ノート

反応式

HRID 851396 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 (3 ml) 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-722e2a9a247049278f71fff9fff0b43f
出典データセット
uspto-grants-1983_05
特許番号
US04383945

反応ノート

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