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

HRID 2078438Notes

Reaction equation

[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

Participants

Conditions

Temperature: 60 °C

Procedure

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.

Workup

filtrationThe mixture was then filtered
concentrationthe filtrate was concentrated in vacuo
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

Sources & evidence

ORD record: ord-cfe74e37c3194bedbadf793b8b22c408
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928225B2

Reaction notes

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