Triethylamine → tert-Butyl trans-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]-5-[(methylsulfonyl)oxy]piperidine-1-carboxylate

HRID 602452노트

반응식

HRID 602452 반응식
[OH:1][CH:2]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]([CH2:15][C:16]2([OH:22])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[OH:22][C:16]1([CH2:15][C@H:5]2[CH2:4][CH2:3][C@H:2]([O:1][S:31]([CH3:30])(=[O:33])=[O:32])[CH2:7][N:6]2[C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[CH2:17][CH2:18][O:19][CH2:20][CH2:21]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67270791HCID 67270791, 화합물

생성물 1

HCID 86624146tert-Butyl trans-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]-5-[(methylsulfonyl)oxy]piperidine-1-carboxylate수율 28.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of tert-butyl 5-hydroxy-2-[(4-hydroxytetrahydro-2H-pyran-4-yl)methyl]piperidine-1-carboxylate (1.92 g, 6.09 mmol, step 2 of Example 2), triethylamine (739 mg, 7.30 mmol) in dichloromethane (27 mL) was added methanesulfonyl chloride (836 mg, 7.30 mmol) at 0° C., and the mixture was allowed to warm to room temperature over 20 h. The mixture was quenched with water (50 mL). The organic layer was separated and the aqueous layer was extracted with dichloromethane (50 mL×3). The combined organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:5) to give 673 mg (28%) of the title compound as a white crystal. (cis isomer, 634 mg, 26% yield)

후처리

  1. customThe mixture was quenched with water (50 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with dichloromethane (50 mL×3)
  4. dry with materialThe combined organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was chromatographed on a column of silica gel eluting with n-hexane/ethyl acetate (1:5)

출처 및 근거

ORD 기록
ord-7b8b8b922287408d85ae8e9b4fb0bdf3
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906532B2

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