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

HRID 2078438ノート

反応式

HRID 2078438 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-cfe74e37c3194bedbadf793b8b22c408
出典データセット
uspto-grants-2011_04
特許番号
US07928225B2

反応ノート

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