Triethylamine → tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

HRID 255389노트

반응식

HRID 255389 반응식
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Br[CH2:16][CH:17]([OH:19])[CH3:18].BrC(C)CO.C(N(CC)CC)C>C(#N)C>[OH:19][CH:17]([CH3:18])[CH2:16][N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 117132-Bromopropan-1-olHCID 297401-Bromo-2-propanolHCID 7238334-(N-Boc-amino)piperidine

생성물 1

HCID 56973353tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
70 °C

실험 절차

tert-Butyl piperidin-4-ylcarbamate (2.0 g, 10.0 mmol), 1-bromopropan-2-ol (2.8 g, 20.0 mmol, commercial product which also contained 30% of the regioisomer 2-bromopropan-1-ol), triethylamine (4.2 mL, 30.0 mmol), and acetonitrile (15 mL) were combined in a microwave vial and heated to 70° C. for 4 hours. The reaction mixture was concentrated to dryness. The crude product was partitioned between ethyl acetate/water. The aqueous phase was re-extracted 2× with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered, and concentrated to dryness. The product was purified by flash chromatography on silica gel eluting with a gradient of 20-30% methanol in dichloromethane to give 1.7 g of the desired product as an oil.

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customThe crude product was partitioned between ethyl acetate/water
  3. extractionThe aqueous phase was re-extracted 2× with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe product was purified by flash chromatography on silica gel eluting with a gradient of 20-30% methanol in dichloromethane

출처 및 근거

ORD 기록
ord-3e11c137c99a4ccb942b1c74a5e055d9
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07875715B2

반응 노트

불러오는 중…