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

HRID 429284노트

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HRID 429284 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 21873804Tetrahydrofuran ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0fb93f4ebc3b4b3b97dc18ca024da03a
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316444B1

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