HCID 59598472、化合物 → (R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate

HRID 253540ノート

反応式

HRID 253540 の反応式
CON(C)[C:4]([C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[CH3:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][Mg]Cl>C1COCC1>[CH3:20][O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:4]([C@@H:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:7]1)=[O:5]

参加物

4

反応物 2

HCID 59598472HCID 59598472、化合物HCID 178495008HCID 178495008、化合物

生成物 1

HCID 59598474(R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a solution of (R)-tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (1.37 g, 5.0 mmol) in THF (10 mL) at −20° C., there was added (4-methoxybutyl)magnesium chloride in THF (1.47 M, 10.2 mL, 15.0 mmol) dropwise such that the temperature remained below −20° C. After addition, the resulting solution was warmed to rt, and quenched with 1 N aq HCl (10 mL). The organic layer was separated, and the aqueous layer was extracted with ether (3×5 mL). The combined organic layers were washed with satd aq NaHCO3 (10 mL) and brine (5 mL), and dried over Na2SO4. The solvent was then removed in vacuo to give (R)-tert-butyl 2-(5-methoxypentanoyl)morpholine-4-carboxylate (1.41 g, 93%), which was used for the next step without purification; MS m/s 324 (M+Na+).

後処理

  1. customremained below −20° C
  2. additionAfter addition
  3. customquenched with 1 N aq HCl (10 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with ether (3×5 mL)
  6. washThe combined organic layers were washed with satd aq NaHCO3 (10 mL) and brine (5 mL)
  7. dry with materialdried over Na2SO4
  8. customThe solvent was then removed in vacuo

出典と根拠

ORDレコード
ord-36657eaff8514535827fb593f8f22f5b
出典データセット
uspto-grants-2011_01
特許番号
US07872028B2

反応ノート

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