Potassium Carbonate → tert-Butyl {3-[7-(3-hydroxypropyl)-9-oxa-3 7-diazabicyclo[3.3.1]non-3-yl]-propyl}carbamate

HRID 2078438노트

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HRID 2078438 반응식
[C:1]([O:5][C:6](=[O:20])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:18][CH:17]2[O:19][CH:13]([CH2:14][NH:15][CH2:16]2)[CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:22][CH2:23][CH2:24][OH:25].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[OH:25][CH2:24][CH2:23][CH2:22][N:15]1[CH2:14][CH:13]2[O:19][CH:17]([CH2:18][N:11]([CH2:10][CH2:9][CH2:8][NH:7][C:6](=[O:20])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:12]2)[CH2:16]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 131728789Tert-butyl[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate

생성물 1

HCID 91166398tert-Butyl {3-[7-(3-hydroxypropyl)-9-oxa-3 7-diazabicyclo[3.3.1]non-3-yl]-propyl}carbamate수율 69.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

To tert-butyl[3-(9-oxa-3,7-diazabicyclo[3.3.1]non-3-yl)propyl]carbamate (0.300 g; 1.05 mmol; see Preparation A above), 3-bromo-1-propanol (0.153 mg; 1.10 mmol) and potassium carbonate (0.218 mg; 1.58 mmol) was added acetonitrile (10 mL). The resulting mixture was heated to 60° C. and stirred overnight. The mixture was then filtered and the filtrate was concentrated in vacuo. The crude product was purified by filtration through silica gel (10 g, Isolute®, eluent: DCM (30 mL), acetonitrile (30 mL), DCM/MeOH 80:20 (140 mL) and DCM/MeOH(NH3-satd.) (40 mL), 10 mL/fraction, product in fractions 8-22), which afforded 250 mg (69.2%) of the title compound.

후처리

  1. filtrationThe mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. filtrationThe crude product was purified by filtration through silica gel (10 g, Isolute®, eluent: DCM (30 mL), acetonitrile (30 mL), DCM/MeOH 80:20 (140 mL) and DCM/MeOH(NH3-satd.) (40 mL), 10 mL/fraction, product in fractions 8-22), which

출처 및 근거

ORD 기록
ord-cfe74e37c3194bedbadf793b8b22c408
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07928225B2

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