Sodium Bicarbonate → tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate

HRID 1807747Notes

Reaction equation

HRID 1807747 reaction equation
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(#N)C>[F:25][C:24]([F:26])([F:27])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]2)=[CH:18][CH:19]=1)([OH:32])[C:28]([F:29])([F:31])[F:30]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Product 1

HCID 86638560tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylateYield 63.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of tert-butyl 1,4-diazepane-1-carboxylate (24.52 mmol, 4.91 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (24.52 mmol, 8.26 g) and sodium hydrogencarbonate (36.8 mmol, 3.09 g) in acetonitrile (100 mL) was stirred for 24 hours then was concentrated under reduced pressure. Dichloromethane was added and the suspension was filtered. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%) to give the title compound (7.1 g). MS (ESI) m/z 457.2 [M+H]+

Workup

  1. concentrationthen was concentrated under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%)

Sources & evidence

ORD record
ord-3c9b728cc4a94539b578c54ab3790306
Source dataset
uspto-grants-2013_01
Patent number
US08357679B2

Reaction notes

Loading…