Sodium borohydride → Benzyl 2-(1-hydroxyethyl)morpholine-4-carboxylate

HRID 429284ノート

反応式

HRID 429284 の反応式
[C:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)(=[O:3])[CH3:2].[BH4-].[Na+]>C1COCC1.CCO>[OH:3][CH:1]([CH:4]1[O:9][CH2:8][CH2:7][N:6]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[O:11])[CH2:5]1)[CH3:2]

参加物

4

反応物 2

HCID 4311764Sodium borohydrideHCID 18354411Phenylmethyl 2-acetyl-4-morpholinecarboxylate

生成物 1

HCID 18354365Benzyl 2-(1-hydroxyethyl)morpholine-4-carboxylate

試薬・触媒・溶媒 1

HCID 21873804Tetrahydrofuran ethanol溶媒

実験手順

To a solution of 1.38 of 2-acetyl-4-benzyloxycarbonylmorpholine in 50 mL of 1:1 THF-EtOH was added 400 mg of sodium borohydride, in several portions. The mixture was stirred at room temperature for 2 h, then quenched by addition of 25 mL of saturated NaHCO3. The mixture was diluted with 75 mL of water and 25 mL of EtOAc. The phases were separated and the aqueous phase was extracted with 2×25 mL of EtOAc. The combined organics were washed with 25 mL of brine, dried over Na2SO4, and concentrated. The residue was purified by flash chromatography, eluting with 2:1 hexanes-EtOAc, to yield 383 mg of diastereomer 1, 341 mg of diastereomer 2, and 436 mg of a mixture of the two isomers. Data for diastereomer 1. Rf 0.35 (1:1 hexanes-EtOAc) 1H NMR (500 MHz, CDCl3): δ7.30-7.43 (m, 4H), 5.12-5.23 (m, 2H), 3.80-4.18 (m, 4H), 3.57 (br t, J=11.0Hz, 1H), 3.32 (br s, 1H), 2.84-3.11 (m, 2H), 2.05 (br s, 1H),1.22 (d, J=6.5 Hz, 3H). Data for diastereomer 2. Rf 0.28 (1:1 hexanes-EtOAc).

後処理

  1. customquenched by addition of 25 mL of saturated NaHCO3
  2. additionThe mixture was diluted with 75 mL of water and 25 mL of EtOAc
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with 2×25 mL of EtOAc
  5. washThe combined organics were washed with 25 mL of brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. customThe residue was purified by flash chromatography
  9. washeluting with 2:1 hexanes-EtOAc

出典と根拠

ORDレコード
ord-0fb93f4ebc3b4b3b97dc18ca024da03a
出典データセット
uspto-grants-2001_11
特許番号
US06316444B1

反応ノート

読み込み中…