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Acetic Acid → 7-{2-[(4-Cyano-benzenesulfonyl)-methyl-amino]-ethyl}-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

HRID 1992354
Notes
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Reaction equation

HRID 1992354 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH3:16])[CH2:13][CH:14]=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#[N:2].[C:17]([O:21][C:22]([N:24]1[CH2:31][CH:30]2[O:32][CH:26]([CH2:27][NH:28][CH2:29]2)[CH2:25]1)=[O:23])([CH3:20])([CH3:19])[CH3:18].C(O)(=O)C.[BH3-]C#N.[Na+]>ClCCl>[C:17]([O:21][C:22]([N:24]1[CH2:25][CH:26]2[O:32][CH:30]([CH2:29][N:28]([CH2:14][CH2:13][N:12]([S:9]([C:6]3[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=3)(=[O:11])=[O:10])[CH3:16])[CH2:27]2)[CH2:31]1)=[O:23])([CH3:20])([CH3:18])[CH3:19]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 185404123-Boc-9-oxa-3,7-diazabicyclo[3.3.1]nonaneHCID 866259934-Cyano-N-methyl-N-(2-oxo-ethyl)-benzenesulfonamide2×

Product 1

HCID 685191317-{2-[(4-Cyano-benzenesulfonyl)-methyl-amino]-ethyl}-9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of step (ii) product 4-Cyano-N-methyl-N-(2-oxo-ethyl)-benzenesulfonamide (4.97 g), and 9-oxa-3,7-diaza-bicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (4.95 g; see WO 01/28992) and acetic acid (1.7 ml) in dry dichloromethane (50 ml) was stirred at RT for 3 h and then cooled to 0° C. NaBH3CN (1.96 g, 0.0312 mol) was added and stirring continued at RT overnight under nitrogen atmosphere. The reaction mixture was quenched with water, extracted with dichloromethane, washed with water and brine and dried over sodium sulfate. Solvent evaporated under reduced pressure and the residue was purified by column chromatography over silica gel using 28% ethyl acetate in petroleum ether eluent to give the sub-title compound (2.2 g) as a liquid.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customSolvent evaporated under reduced pressure
  6. customthe residue was purified by column chromatography over silica gel using 28% ethyl acetate in petroleum ether eluent

Sources & evidence

ORD record
ord-87cf067e08ae4f2abec07e760bf521be
Source dataset
uspto-grants-2010_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07648985B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes